NPASS Compound

Natural Product: NPC138303

Natural Product ID	NPC138303
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GKQDCRVVJYVECB-LKUYUNCQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL443672
PubChem CID	21588199
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

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 83 86 0 0 0 0 0 0 0 0999 V2000 7.6276 -1.4884 -0.5694 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2614 -0.4579 0.5328 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3995 -1.1656 1.4937 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9206 -0.4328 2.6828 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0120 0.7151 2.4639 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5560 1.7943 1.6816 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0078 2.2509 0.5883 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7935 1.7212 0.0438 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2443 2.2061 -1.0840 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0091 1.6563 -1.6249 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5534 2.1595 -2.6817 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3359 0.6267 -1.0338 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1285 0.0520 -1.5168 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2768 -1.4171 -1.7012 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7563 -2.0657 -1.1831 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7003 -1.0793 -0.5978 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9109 0.1118 -0.3907 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1220 -0.0514 0.7898 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4004 1.4772 -0.3250 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7763 1.7380 1.0407 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1387 2.6487 1.8356 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1674 3.2978 1.3495 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5285 2.9119 3.2355 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5151 1.9568 -1.1388 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6794 1.3579 -1.4465 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9950 0.0630 -0.9305 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8509 -0.8097 -1.4606 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9871 -1.2119 -2.5593 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1054 -0.7865 -1.1331 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7520 -2.1167 -0.5801 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6728 -2.4192 0.2923 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4344 -1.6888 0.6052 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4555 -2.6260 1.2830 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9630 -1.3642 -0.0309 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8374 -0.6349 1.2793 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3491 -1.8075 -0.3622 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4228 3.3339 -1.7587 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3085 3.3175 -2.5954 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4668 -2.0197 -2.3928 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3148 -2.2154 -0.0803 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1530 -0.9424 -1.3565 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7013 -1.9741 -0.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2154 -0.1199 1.0065 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7745 0.3835 0.0515 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9496 -2.0999 1.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5219 -1.6132 0.9049 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4724 -1.1465 3.4505 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8440 0.0177 3.2126 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6969 1.1165 3.5044 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0529 0.2861 2.0707 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4982 2.2603 2.0366 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4760 3.0826 0.0336 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2465 0.9169 0.4862 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7689 3.0135 -1.5524 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2240 0.5436 -2.4373 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8328 -3.1520 -1.2182 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7236 0.1959 1.5369 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5390 2.1602 -0.5107 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4457 2.3835 3.5204 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6229 4.0288 3.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6927 2.5767 3.9082 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3499 1.9140 -2.1004 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9307 0.1530 0.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6211 -0.7365 -2.1101 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1126 -2.9656 -1.2493 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1290 -2.6110 1.3260 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3011 -3.4801 0.0660 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5494 -0.8337 1.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6778 -2.6451 2.3684 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6436 -3.6435 0.8756 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4050 -2.3826 1.0543 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6456 -0.9842 1.9823 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8963 -0.7828 1.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0741 0.4402 1.0870 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0524 -1.0818 0.0383 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5086 -1.9577 -1.4533 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5362 -2.7849 0.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1885 4.0101 -0.9102 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3421 3.5865 -2.2790 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5689 3.8481 -2.2313 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2467 -1.9777 -3.4782 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3864 -1.4711 -2.1797 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5304 -3.0691 -2.0610 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 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 16 15 1 6 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 19 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 2 0 26 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 30 34 1 0 34 35 1 0 34 36 1 0 24 37 1 0 37 38 1 0 14 39 1 0 17 13 1 0 34 29 1 0 32 16 1 0 27 16 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 0 2 44 1 0 3 45 1 0 3 46 1 0 4 47 1 0 4 48 1 0 5 49 1 0 5 50 1 0 6 51 1 0 7 52 1 0 8 53 1 0 9 54 1 0 13 55 1 6 15 56 1 0 18 57 1 0 19 58 1 6 23 59 1 0 23 60 1 0 23 61 1 0 25 62 1 0 26 63 1 1 29 64 1 6 30 65 1 6 31 66 1 0 31 67 1 0 32 68 1 1 33 69 1 0 33 70 1 0 33 71 1 0 35 72 1 0 35 73 1 0 35 74 1 0 36 75 1 0 36 76 1 0 36 77 1 0 37 78 1 0 37 79 1 0 38 80 1 0 39 81 1 0 39 82 1 0 39 83 1 0 M END

Standard InCHIKey	GKQDCRVVJYVECB-LKUYUNCQSA-N
Standard InCHI	InChI=1S/C32H44O7/c1-7-8-9-10-11-12-13-14-25(35)39-28-19(2)17-31-20(3)15-24-26(30(24,5)6)23(27(31)36)16-22(18-33)29(32(28,31)37)38-21(4)34/h11-14,16-17,20,23-24,26,28-29,33,37H,7-10,15,18H2,1-6H3/b12-11-,14-13+/t20-,23+,24-,26+,28+,29-,31+,32-/m1/s1
SMILES	CCCCC/C=CC=CC(=O)O[C@H]1C(=C[C@]23[C@]1(O)[C@H](OC(=O)C)C(=C[C@H](C3=O)[C@H]1[C@@H](C[C@H]2C)C1(C)C)CO)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	540.31	Volume:	570.879 ? Van der Waals volume.
Dense:	0.946	LogP:	4.631 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.048 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.21 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	23.0
TPSA:	110.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.144	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.302	Fsp³:	0.656
MCE-18:	108.075 ? 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:	0.551	Fluc inhibitor:	0.042 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.072 ? 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:	0.29	Promiscuous compounds:	0.432

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.27	MDCK Permeability:	-4.908
Pgp-inhibitor:	0.855	Pgp-substrate:	0.339
PAMPA:	0.016 ? 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):	0.022
20% Bioavailability (F20%):	0.523	30% Bioavailability (F30%):	0.988
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021	MRP1:	0.717
Plasma Protein Binding (PPB):	93.859%	Volume Distribution (VD):	0.113
Fu:	5.263% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.927
OATP1B3 inhibitor:	0.887	BCRP inhibitor:	0.018
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.997
CYP2C19-inhibitor:	0.234	CYP2C19-substrate:	0.273
CYP2C9-inhibitor:	0.782	CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.303
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.988 ? 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):

7.108

Half-life (T1/2):

0.843

ADMET: Toxicity

hERG Blockers:	0.121	hERG Blockers (10um):	0.367
Human Hepatotoxicity (H-HT):	0.733	Drug-induced Liver Injury (DILI):	0.185
AMES Toxicity:	0.576	Rat Oral Acute Toxicity:	0.238
Maximum Recommended Daily Dose:	0.533	Skin Sensitization:	1.0
Carcinogencity:	0.415	Eye Corrosion:	0.025
Eye Irritation:	0.652	Respiratory Toxicity:	0.418
Drug-induced Neurotoxicity:	0.039	Ototoxicity:	0.662
Hematotoxicity:	0.226	Drug-induced Nephrotoxicity:	0.833
Genotoxicity:	0.033	RPMI-8226 Immunitoxicity:	0.109
A549 Cytotoxicity:	0.671	Hek293 Cytotoxicity:	0.697
BCF:	1.78 ? 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:	4.916 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.673 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.185 ? 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
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[12350140]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12762796]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387657]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[1955882]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	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
Activity	1

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	Activity	>	75.0	%	DrugMatrix in vivo data: Pathology

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 NPC138303 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	19037
0.1-0.2	28302
0.2-0.3	2390
0.3-0.4	100
0.4-0.5	10
0.5-0.6	9
0.6-0.7	7
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	Natural Product ID
0.7222	Intermediate Similarity	NPC46269
0.7222	Intermediate Similarity	NPC106395
0.7222	Intermediate Similarity	NPC138757
0.6944	Remote Similarity	NPC47951
0.6711	Remote Similarity	NPC67290
0.6711	Remote Similarity	NPC133677
0.6364	Remote Similarity	NPC482242
0.6364	Remote Similarity	NPC482243
0.6	Remote Similarity	NPC75898
0.6	Remote Similarity	NPC221349
0.5844	Remote Similarity	NPC482240
0.5844	Remote Similarity	NPC482239
0.5467	Remote Similarity	NPC607683
0.5395	Remote Similarity	NPC267734
0.5395	Remote Similarity	NPC308191
0.5395	Remote Similarity	NPC38423
0.5395	Remote Similarity	NPC482241
0.5375	Remote Similarity	NPC123855
0.5375	Remote Similarity	NPC76550

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC138303 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6968
0.1-0.2	2145
0.2-0.3	36
0.3-0.4	0
0.4-0.5	1
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