NPASS Compound

Natural Product: NPC488158

Natural Product ID	NPC488158
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WVWARXGTPSCHDN-AHIYZFNLSA-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]

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 80 86 0 0 0 0 0 0 0 0999 V2000 -4.7595 0.7014 1.3507 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0641 -0.0775 0.2500 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0629 -0.5728 -0.7662 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7454 0.1399 -2.0628 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2131 0.3154 -1.8938 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2347 0.9159 -0.5308 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9384 1.1096 0.1405 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1667 2.3207 -0.3509 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0413 2.4901 0.6530 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8878 1.3344 0.4449 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1314 1.3976 1.3076 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1084 0.4462 0.7144 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5875 -0.9316 0.4782 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1684 -1.0320 0.0804 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2570 -0.0016 0.7166 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2787 -0.2448 2.1855 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -1.2041 2.6743 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1265 -0.1438 0.1560 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8863 -1.0630 1.1236 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2993 -1.2486 0.7758 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9810 -1.6895 1.9348 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4190 -1.4897 -0.5107 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7438 -1.4344 -0.1974 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5266 -1.4718 -1.5150 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9236 -0.9906 -1.3663 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0632 0.2372 -0.5108 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8884 1.3215 -1.1664 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1425 0.8234 -1.5129 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8076 0.7260 -0.1608 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2066 -0.2975 0.6087 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2895 0.3064 1.4261 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5476 -2.7821 -1.9896 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0720 -2.6491 0.4496 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9650 2.1107 -0.6195 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4698 -0.4778 -0.3729 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3491 0.2265 -1.1008 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6299 0.1111 -0.4357 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7400 0.6266 -0.7908 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4720 -0.6715 0.6886 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1564 -1.1202 0.7710 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7441 1.0643 1.0278 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7362 0.1940 2.3163 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1595 1.6508 1.5171 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8721 -1.6645 -0.9771 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9588 -0.4986 -2.9425 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1541 1.1417 -2.1426 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8391 -0.7300 -1.9266 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8102 0.9574 -2.6807 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1646 1.3443 1.2260 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8436 3.1719 -0.3936 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7509 2.0853 -1.3658 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5210 3.4170 0.4994 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5046 2.4123 1.6558 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2079 1.3373 -0.6174 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5805 2.4053 1.3108 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8860 1.1091 2.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4074 0.8649 -0.2915 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7519 -1.5923 1.3796 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7816 -2.0526 0.3212 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0462 -0.9285 -1.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2130 0.4218 2.8913 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0281 -0.6096 -0.8451 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3933 -2.0433 1.1946 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8064 -0.5799 2.1191 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 -2.1047 0.0617 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5261 -2.5031 2.3079 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0057 -0.8647 -2.2910 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6241 -1.8056 -1.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2865 -0.6979 -2.3944 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5937 -0.0619 0.4202 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3789 1.8239 -1.9919 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0657 2.0944 -0.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6344 1.4084 -2.1111 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0438 -0.6586 1.2768 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4584 -3.1643 -1.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7374 -2.5004 1.1643 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6878 2.5366 -1.4730 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1855 0.7850 -2.0079 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1574 -2.2552 0.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6876 -0.9767 1.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 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 1 0 14 15 1 0 15 16 1 1 16 17 2 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 13 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 29 30 1 0 30 31 1 0 24 32 1 0 23 33 1 1 6 34 1 6 3 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 20 2 1 0 30 23 1 0 40 35 1 0 6 2 1 0 18 7 1 0 15 10 1 0 31 12 1 0 1 41 1 0 1 42 1 0 1 43 1 0 3 44 1 6 4 45 1 0 4 46 1 0 5 47 1 0 5 48 1 0 7 49 1 1 8 50 1 0 8 51 1 0 9 52 1 0 9 53 1 0 10 54 1 6 11 55 1 0 11 56 1 0 12 57 1 6 13 58 1 1 14 59 1 0 14 60 1 0 16 61 1 0 18 62 1 6 19 63 1 0 19 64 1 0 20 65 1 6 21 66 1 0 24 67 1 6 25 68 1 0 25 69 1 0 26 70 1 1 27 71 1 0 27 72 1 0 28 73 1 0 30 74 1 1 32 75 1 0 33 76 1 0 34 77 1 0 36 78 1 0 40 79 1 0 40 80 1 0 M END

Standard InCHIKey	WVWARXGTPSCHDN-AHIYZFNLSA-N
Standard InCHI	InChI=1S/C29H40O11/c1-26-17(14-6-24(34)37-12-14)4-5-28(26,35)18-3-2-15-7-20-21(10-27(15,13-31)19(18)9-22(26)32)40-29(36)23(33)8-16(11-30)38-25(29)39-20/h6,13,15-23,25,30,32-33,35-36H,2-5,7-12H2,1H3/t15-,16-,17+,18+,19-,20+,21+,22+,23+,25-,26-,27+,28-,29-/m0/s1
SMILES	C[C@]12[C@H](CC[C@@]2([C@@H]2CC[C@H]3C[C@@H]4[C@@H](C[C@]3(C=O)[C@H]2C[C@H]1O)O[C@]1([C@@H](C[C@@H](CO)O[C@H]1O4)O)O)O)C1=CC(=O)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	564.26	Volume:	539.028 ? Van der Waals volume.
Dense:	1.047	LogP:	0.361 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.024 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.534 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	37.0
TPSA:	172.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	5.0	Rings:	7.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.177	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.849	Fsp³:	0.862
MCE-18:	128.333 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.499	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.159	Promiscuous compounds:	0.843

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.933	MDCK Permeability:	-5.175
Pgp-inhibitor:	0.0	Pgp-substrate:	0.994
PAMPA:	0.998 ? 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):	0.024
20% Bioavailability (F20%):	0.887	30% Bioavailability (F30%):	0.943
50% Bioavailability (F50%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	0.744
Plasma Protein Binding (PPB):	50.617%	Volume Distribution (VD):	-0.215
Fu:	50.151% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.984
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.001
BSEP inhibitor:	0.05

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.001 ? 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):

2.305

Half-life (T1/2):

2.926

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.124
Human Hepatotoxicity (H-HT):	0.886	Drug-induced Liver Injury (DILI):	0.881
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.94
Maximum Recommended Daily Dose:	0.979	Skin Sensitization:	1.0
Carcinogencity:	0.994	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.802
Drug-induced Neurotoxicity:	0.78	Ototoxicity:	0.934
Hematotoxicity:	0.867	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.778
A549 Cytotoxicity:	0.979	Hek293 Cytotoxicity:	0.978
BCF:	0.525 ? 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:	3.298 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.007 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.126 ? 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
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	roots	Wadi Um Hebal, Egypt	2001-JAN	PMID[16989527]
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19555122]
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30629433]
NPO33139	Pergularia tomentosa	Species	Apocynaceae	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

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell line	5

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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	300.0	nM	PMID[30629433]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	8900.0	nM	PMID[30629433]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	2000.0	nM	PMID[30629433]
NPT1307	Cell line	Calu-1	Homo sapiens	IC50	=	3700.0	nM	PMID[30629433]
NPT380	Cell line	U-251	Homo sapiens	IC50	=	5500.0	nM	PMID[30629433]

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 NPC488158 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	16861
0.1-0.2	31161
0.2-0.3	1601
0.3-0.4	144
0.4-0.5	56
0.5-0.6	16
0.6-0.7	7
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC488159
0.875	High Similarity	NPC488162
0.875	High Similarity	NPC93416
0.8537	High Similarity	NPC475136
0.8072	Intermediate Similarity	NPC488161
0.8072	Intermediate Similarity	NPC16569
0.7558	Intermediate Similarity	NPC474466
0.7209	Intermediate Similarity	NPC488160
0.7093	Intermediate Similarity	NPC253456
0.7093	Intermediate Similarity	NPC159338
0.7045	Intermediate Similarity	NPC329905
0.6923	Remote Similarity	NPC225385
0.6739	Remote Similarity	NPC488163
0.6404	Remote Similarity	NPC104585
0.6374	Remote Similarity	NPC42670
0.6374	Remote Similarity	NPC19124
0.6264	Remote Similarity	NPC277374
0.6064	Remote Similarity	NPC157817
0.5806	Remote Similarity	NPC171619
0.5625	Remote Similarity	NPC609258
0.5476	Remote Similarity	NPC189588
0.5465	Remote Similarity	NPC196471
0.5464	Remote Similarity	NPC91
0.5464	Remote Similarity	NPC79193
0.5417	Remote Similarity	NPC179412
0.5417	Remote Similarity	NPC471356
0.5385	Remote Similarity	NPC476221
0.5385	Remote Similarity	NPC477709
0.5354	Remote Similarity	NPC163365
0.5294	Remote Similarity	NPC480905
0.5294	Remote Similarity	NPC470094
0.5169	Remote Similarity	NPC475030
0.5146	Remote Similarity	NPC85369
0.5096	Remote Similarity	NPC473040

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488158 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6625
0.1-0.2	2487
0.2-0.3	24
0.3-0.4	7
0.4-0.5	7
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