NPASS Compound

Natural Product: NPC40703

Natural Product ID	NPC40703
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MDCXDLDKQKBOES-XOMSRXTOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101998586
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

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 78 82 0 0 0 0 0 0 0 0999 V2000 2.0730 3.1757 -0.5099 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5650 2.0750 0.0270 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3348 0.9005 -0.8247 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1598 0.5186 -0.8457 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4997 -0.0526 0.4731 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8832 -0.4922 0.7415 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9408 0.5349 0.6532 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2472 0.0996 0.6922 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5939 -1.3255 0.8239 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4016 -2.2499 0.7820 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8108 -3.5509 0.2374 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2888 -4.0289 -0.7794 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8030 -4.2690 0.8677 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2423 -5.5434 0.3822 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3293 -1.6395 -0.0375 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0761 1.1783 0.6041 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4671 1.3224 0.5944 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0469 2.5474 0.4938 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2379 3.6683 0.3995 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8650 3.5414 0.4077 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2658 2.2838 0.5110 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9838 1.8733 0.5429 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2689 -0.4021 -2.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6455 -1.3558 -2.0689 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6434 -1.4434 -1.0768 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1036 -0.3146 -0.3820 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4459 -0.0426 -0.6655 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2628 -0.0629 0.4602 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2910 -1.1436 0.2374 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6173 -0.8521 0.8609 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4959 0.1433 1.9831 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6935 1.3435 1.6244 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5802 2.5447 1.3441 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7411 3.6537 1.2468 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8088 1.1933 0.6038 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0703 -0.4512 3.1664 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4802 -0.4124 -0.1401 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7869 -2.3055 0.8470 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3017 -0.2164 -2.9836 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1415 0.7105 -2.8593 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4179 -1.0356 -4.0949 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4692 -0.7952 -5.0352 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3230 3.2295 -1.5654 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2603 4.0639 0.0733 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3356 2.0748 1.0748 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6198 1.0795 -1.8901 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7181 1.4593 -1.0101 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1448 -0.9845 0.5925 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1332 0.5889 1.3197 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9245 -0.8699 1.8181 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3119 -1.5687 -0.0107 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1769 -1.4549 1.7616 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9850 -2.3153 1.8057 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6591 -6.0791 1.2788 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3435 -6.0776 0.0155 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0241 -5.4617 -0.3732 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8422 -1.2256 -0.8812 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0706 0.4148 0.6707 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1395 2.6135 0.4902 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7430 4.6205 0.3213 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2400 4.4282 0.3331 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1485 2.5015 0.4975 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6083 -2.0545 -2.8924 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0798 -0.4739 0.7269 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6245 -0.2972 1.3343 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3669 -1.3934 -0.8476 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0916 -1.7800 1.2821 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5495 0.4970 2.1910 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0986 1.6276 2.5425 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1477 2.4486 0.4173 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2293 2.7200 2.2429 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0273 3.6290 1.9496 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6314 -0.2145 3.9387 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0249 0.1213 -0.8331 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6085 -3.0272 0.2247 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2099 -0.0870 -4.6338 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0398 -0.3346 -5.9457 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9593 -1.7407 -5.3233 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 10 15 1 0 8 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 4 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 29 38 1 0 23 39 1 0 39 40 2 0 39 41 1 0 41 42 1 0 26 3 1 0 35 28 1 0 15 6 1 0 21 16 1 0 22 7 1 0 1 43 1 0 1 44 1 0 2 45 1 0 3 46 1 6 4 47 1 6 5 48 1 0 5 49 1 0 6 50 1 1 9 51 1 0 9 52 1 0 10 53 1 1 14 54 1 0 14 55 1 0 14 56 1 0 15 57 1 0 17 58 1 0 18 59 1 0 19 60 1 0 20 61 1 0 22 62 1 0 24 63 1 0 26 64 1 1 28 65 1 1 29 66 1 6 30 67 1 1 31 68 1 1 32 69 1 1 33 70 1 0 33 71 1 0 34 72 1 0 36 73 1 0 37 74 1 0 38 75 1 0 42 76 1 0 42 77 1 0 42 78 1 0 M END

Standard InCHIKey	MDCXDLDKQKBOES-XOMSRXTOSA-N
Standard InCHI	InChI=1S/C29H36N2O11/c1-4-13-15(9-19-22-16(10-20(30-19)27(37)39-3)14-7-5-6-8-18(14)31-22)17(26(36)38-2)12-40-28(13)42-29-25(35)24(34)23(33)21(11-32)41-29/h4-8,12-13,15,19-21,23-25,28-35H,1,9-11H2,2-3H3/t13-,15+,19+,20+,21-,23-,24+,25-,28+,29+/m1/s1
SMILES	C=C[C@@H]1[C@H](C[C@H]2c3c(C[C@@H](C(=O)OC)N2)c2ccccc2[nH]3)C(=CO[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	588.23	Volume:	564.952 ? Van der Waals volume.
Dense:	1.041	LogP:	0.672 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.159 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.698 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	30.0
TPSA:	189.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.178	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.052	Fsp³:	0.517
MCE-18:	112.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.523	Fluc inhibitor:	0.02 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.555 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.105 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.015	Promiscuous compounds:	0.466

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.885	MDCK Permeability:	-5.171
Pgp-inhibitor:	0.01	Pgp-substrate:	0.972
PAMPA:	0.473 ? 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):	0.007
20% Bioavailability (F20%):	0.095	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.89
Plasma Protein Binding (PPB):	78.027%	Volume Distribution (VD):	-0.595
Fu:	21.574% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.085
BSEP inhibitor:	0.062

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.232
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.212
CYP3A4-inhibitor:	0.009	CYP3A4-substrate:	0.975
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.416 ? 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):

2.468

Half-life (T1/2):

1.994

ADMET: Toxicity

hERG Blockers:	0.091	hERG Blockers (10um):	0.169
Human Hepatotoxicity (H-HT):	0.906	Drug-induced Liver Injury (DILI):	0.985
AMES Toxicity:	0.978	Rat Oral Acute Toxicity:	0.433
Maximum Recommended Daily Dose:	0.822	Skin Sensitization:	0.999
Carcinogencity:	0.236	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.177
Drug-induced Neurotoxicity:	0.422	Ototoxicity:	0.99
Hematotoxicity:	0.662	Drug-induced Nephrotoxicity:	0.993
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.171
A549 Cytotoxicity:	0.751	Hek293 Cytotoxicity:	0.352
BCF:	0.58 ? 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:	3.328 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.05 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.206 ? 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
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869194]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18588343]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331340]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27700077]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28225280]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31789520]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31804070]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	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

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell line	3

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
NPT81	Cell line	A549	Homo sapiens	IC50	>	80000.0	nM	PMID[31804070]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	80000.0	nM	PMID[31804070]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	80000.0	nM	PMID[31804070]

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 NPC40703 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	15921
0.1-0.2	30974
0.2-0.3	2692
0.3-0.4	196
0.4-0.5	56
0.5-0.6	12
0.6-0.7	3
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
0.8065	Intermediate Similarity	NPC82070
0.7653	Intermediate Similarity	NPC201287
0.7653	Intermediate Similarity	NPC475271
0.7653	Intermediate Similarity	NPC601145
0.6832	Remote Similarity	NPC599983
0.6667	Remote Similarity	NPC474905
0.6132	Remote Similarity	NPC603178
0.578	Remote Similarity	NPC486444
0.578	Remote Similarity	NPC486448
0.578	Remote Similarity	NPC649
0.5727	Remote Similarity	NPC199607
0.5727	Remote Similarity	NPC54591
0.5714	Remote Similarity	NPC180804
0.5714	Remote Similarity	NPC227138
0.5714	Remote Similarity	NPC174788
0.5596	Remote Similarity	NPC476114
0.5357	Remote Similarity	NPC84073
0.5227	Remote Similarity	NPC117596
0.5043	Remote Similarity	NPC486463

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC40703 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4898
0.1-0.2	4145
0.2-0.3	103
0.3-0.4	4
0.4-0.5	0
0.5-0.6	0
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
		NPD

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