NPASS Compound

Natural Product: NPC199607

Natural Product ID	NPC199607
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FCECVXQMCZMWDG-DCMQMPOPSA-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:0000279] Alkaloids and derivatives [CHEMONTID:0001786] Yohimbine alkaloids

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 73 78 0 0 0 0 0 0 0 0999 V2000 0.9131 5.9638 -0.5022 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8162 4.5782 -0.3447 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0390 4.0678 0.6812 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5498 4.8845 1.4315 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0961 2.6357 0.8899 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8373 2.1616 1.8680 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8981 0.7864 1.9766 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0948 -0.0111 0.7872 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3642 0.5596 -0.3920 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6013 1.6651 0.0171 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7414 0.9785 0.7506 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4021 0.0741 -0.2638 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7170 -0.4090 0.1818 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1377 -1.7106 -0.0435 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2477 -2.6623 -0.7554 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2491 -1.8450 -1.5470 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5011 -1.0231 -0.6161 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3405 -0.4749 -1.2398 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6683 -1.4624 -1.7044 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7146 -0.7031 -2.2812 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4025 -1.8511 0.4893 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3212 -2.8662 0.5833 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5374 -2.7399 1.1794 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8737 -1.5082 1.7281 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9662 -0.4736 1.6454 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7402 -0.6287 1.0356 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7107 0.1855 0.8265 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4878 0.0344 0.5948 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1251 -1.1519 0.8450 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0347 -1.0784 2.0579 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2479 -0.2536 1.7852 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9369 -0.7323 0.5222 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9599 -0.9986 -0.5853 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7766 0.2767 -1.3557 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0783 0.7698 -1.6121 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8133 -1.6447 -0.2254 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7381 -1.8367 0.8167 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0340 1.1041 1.7727 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4361 -2.3691 2.3749 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2521 6.3736 -1.2980 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9541 6.2673 -0.7891 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6369 6.5213 0.4322 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3710 2.7795 2.5527 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7498 -1.0192 1.0973 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1167 1.0513 -1.0525 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9833 2.1257 -0.8902 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4669 1.6946 1.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3647 0.3479 1.5901 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4926 0.6840 -1.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8278 -3.2646 -1.5093 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7536 -3.3819 -0.0921 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8711 -1.1516 -2.1853 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6550 -2.4365 -2.2338 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6949 0.0774 -2.1498 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0895 -2.1214 -0.9486 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3200 -2.1127 -2.5334 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5341 -0.5442 -3.2454 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0695 -3.8420 0.1553 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2711 -3.5260 1.2625 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8472 -1.3742 2.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2447 0.4758 2.0772 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6903 1.1972 1.1417 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3436 -1.9192 1.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4989 -0.6726 2.9430 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9801 -0.4545 2.6202 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6216 0.0746 0.1912 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4997 -1.6981 -1.2941 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2420 1.0679 -0.8219 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3432 0.0494 -2.3717 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0377 1.6008 -2.1599 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5498 -1.4968 1.2602 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1327 1.3902 1.5530 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0116 -3.0538 1.7981 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 3 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 14 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 8 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 34 35 1 0 33 36 1 0 32 37 1 0 31 38 1 0 30 39 1 0 10 5 1 0 17 12 1 0 26 21 1 0 36 29 1 0 18 9 1 0 27 13 1 0 1 40 1 0 1 41 1 0 1 42 1 0 6 43 1 0 8 44 1 1 9 45 1 6 10 46 1 6 11 47 1 0 11 48 1 0 12 49 1 6 15 50 1 0 15 51 1 0 16 52 1 0 16 53 1 0 18 54 1 6 19 55 1 0 19 56 1 0 20 57 1 0 22 58 1 0 23 59 1 0 24 60 1 0 25 61 1 0 27 62 1 0 29 63 1 1 30 64 1 1 31 65 1 1 32 66 1 6 33 67 1 6 34 68 1 0 34 69 1 0 35 70 1 0 37 71 1 0 38 72 1 0 39 73 1 0 M END

Standard InCHIKey	FCECVXQMCZMWDG-DCMQMPOPSA-N
Standard InCHI	InChI=1S/C27H34N2O10/c1-36-25(35)15-11-37-26(39-27-24(34)23(33)22(32)19(10-31)38-27)20-14(15)8-17-21-13(6-7-29(17)18(20)9-30)12-4-2-3-5-16(12)28-21/h2-5,11,14,17-20,22-24,26-28,30-34H,6-10H2,1H3/t14-,17+,18+,19-,20+,22-,23+,24-,26+,27+/m1/s1
SMILES	COC(=O)C1=CO[C@H]([C@H]2[C@@H]1C[C@H]1c3c(CCN1[C@H]2CO)c1ccccc1[nH]3)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	546.22	Volume:	518.286 ? Van der Waals volume.
Dense:	1.054	LogP:	0.198 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.754 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.374 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	32.0
TPSA:	174.17 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.262	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.929	Fsp³:	0.593
MCE-18:	126.163 ? 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:	0.529	Fluc inhibitor:	0.032 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.421 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.029 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.005	Promiscuous compounds:	0.212

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.047	MDCK Permeability:	-5.325
Pgp-inhibitor:	0.0	Pgp-substrate:	0.483
PAMPA:	0.97 ? 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%):	0.002	30% Bioavailability (F30%):	0.467
50% Bioavailability (F50%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.231	MRP1:	0.718
Plasma Protein Binding (PPB):	70.537%	Volume Distribution (VD):	-0.548
Fu:	35.247% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.282
BSEP inhibitor:	0.13

ADMET: Metabolism

CYP1A2-inhibitor:	0.025	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.977	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.937
HLM stability:	0.0 ? 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):

2.514

Half-life (T1/2):

2.702

ADMET: Toxicity

hERG Blockers:	0.079	hERG Blockers (10um):	0.168
Human Hepatotoxicity (H-HT):	0.746	Drug-induced Liver Injury (DILI):	0.849
AMES Toxicity:	0.89	Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.188	Skin Sensitization:	1.0
Carcinogencity:	0.315	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.131
Drug-induced Neurotoxicity:	0.053	Ototoxicity:	0.989
Hematotoxicity:	0.502	Drug-induced Nephrotoxicity:	0.947
Genotoxicity:	0.727	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.106	Hek293 Cytotoxicity:	0.257
BCF:	0.488 ? 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:	3.271 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.051 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.057 ? 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 NPC199607 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	18058
0.1-0.2	29387
0.2-0.3	2095
0.3-0.4	224
0.4-0.5	66
0.5-0.6	20
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC54591
0.77	Intermediate Similarity	NPC486444
0.77	Intermediate Similarity	NPC649
0.6389	Remote Similarity	NPC486448
0.6262	Remote Similarity	NPC52254
0.6262	Remote Similarity	NPC611036
0.5872	Remote Similarity	NPC82070
0.5766	Remote Similarity	NPC474905
0.5727	Remote Similarity	NPC40703
0.5625	Remote Similarity	NPC599983
0.5614	Remote Similarity	NPC201287
0.5614	Remote Similarity	NPC475271
0.5614	Remote Similarity	NPC601145
0.5347	Remote Similarity	NPC273374
0.5196	Remote Similarity	NPC486449
0.5196	Remote Similarity	NPC63199
0.5196	Remote Similarity	NPC111602
0.5196	Remote Similarity	NPC102338
0.5196	Remote Similarity	NPC196251
0.5192	Remote Similarity	NPC312870
0.5192	Remote Similarity	NPC199851
0.5192	Remote Similarity	NPC294909
0.5192	Remote Similarity	NPC254240
0.5192	Remote Similarity	NPC128265
0.5192	Remote Similarity	NPC604675
0.5172	Remote Similarity	NPC603178

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC199607 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4603
0.1-0.2	4440
0.2-0.3	99
0.3-0.4	4
0.4-0.5	2
0.5-0.6	2
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
0.5192	Remote Similarity	NPD4500	Approved
0.5192	Remote Similarity	NPD4501	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