NPASS Compound

Natural Product: NPC102996

Natural Product ID	NPC102996
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Taxuyunnanine C
IUPAC Name	n.a.
Synonyms	taxuyunnanine C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL436993
PubChem CID	5321771
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

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 76 78 0 0 0 0 0 0 0 0999 V2000 5.1443 -2.3843 -2.7576 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9135 -1.2359 -1.8616 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9134 -0.6724 -1.3466 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6534 -0.7420 -1.5547 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4523 0.3583 -0.6949 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7829 1.4893 -1.4031 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8499 2.2596 -0.6111 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1633 1.6336 0.5985 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0906 0.2018 0.3559 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5899 -0.1327 0.4324 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2128 -0.7507 1.3640 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3576 -0.8169 1.0111 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7747 -2.0756 0.4144 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1541 -3.1864 1.0763 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1646 -3.2207 2.3135 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5622 -4.3764 0.2475 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1166 -1.0186 0.8213 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5068 -1.6717 -0.4810 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6359 -2.5100 -0.3506 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6767 -3.8437 -0.5764 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6411 -4.4177 -0.9331 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9166 -4.6076 -0.4058 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7922 -0.7364 -1.6039 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8203 0.6976 -1.2082 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6773 1.1122 0.0427 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1813 2.4915 0.0350 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0492 2.5143 0.9139 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1109 3.3624 0.6941 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4283 4.5574 0.0945 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8900 4.8408 -1.0008 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3795 5.5253 0.6871 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0072 0.1260 1.0843 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8514 0.5735 2.5006 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4656 -0.2105 0.9097 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0037 1.6918 -2.2973 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1264 1.8359 1.8305 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3380 -3.2794 -2.1038 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2960 -2.5886 -3.4309 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0976 -2.2033 -3.2971 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4490 0.6910 -0.3637 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2499 1.0434 -2.2938 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5549 2.1627 -1.8709 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0303 2.6436 -1.2738 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3734 3.2183 -0.2809 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9361 0.0792 -0.7819 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3111 -0.8855 1.2869 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7819 -1.1597 2.2791 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5570 -0.9286 2.0883 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5305 -4.7761 0.6598 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7722 -5.1443 0.2377 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7709 -4.0920 -0.7862 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3905 -1.8005 1.5946 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6661 -2.3382 -0.8058 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7413 -5.6871 -0.2308 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5769 -4.4706 -1.3042 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5362 -4.2468 0.4532 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0772 -0.8944 -2.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7907 -0.9302 -2.0988 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9010 2.9352 -0.9043 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4233 3.5835 0.7929 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2347 2.5402 2.0095 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2290 5.5528 1.8017 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4236 5.1821 0.4728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2816 6.5352 0.2727 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4725 -0.1541 3.1166 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8272 0.4096 2.9159 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2867 1.5517 2.7321 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0334 0.5752 1.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7466 -1.1664 1.3877 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8345 -0.0998 -0.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4901 1.1612 -3.1464 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7293 2.4828 -2.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0506 2.0697 -2.7206 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0386 2.8781 2.2002 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1618 1.7032 1.5101 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7931 1.1859 2.6568 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 2 0 9 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 12 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 18 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 25 32 1 0 32 33 1 0 32 34 1 0 24 35 1 0 8 36 1 1 10 5 1 0 32 17 1 0 27 8 1 0 1 37 1 0 1 38 1 0 1 39 1 0 5 40 1 1 6 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 9 45 1 6 11 46 1 0 11 47 1 0 12 48 1 1 16 49 1 0 16 50 1 0 16 51 1 0 17 52 1 1 18 53 1 6 22 54 1 0 22 55 1 0 22 56 1 0 23 57 1 0 23 58 1 0 26 59 1 6 27 60 1 0 27 61 1 0 31 62 1 0 31 63 1 0 31 64 1 0 33 65 1 0 33 66 1 0 33 67 1 0 34 68 1 0 34 69 1 0 34 70 1 0 35 71 1 0 35 72 1 0 35 73 1 0 36 74 1 0 36 75 1 0 36 76 1 0 M END

Standard InCHIKey	KFFHSFCOKCGBBW-VCPDXWRASA-N
Standard InCHI	InChI=1S/C28H40O8/c1-14-12-21(34-17(4)30)25-26(36-19(6)32)24-15(2)20(33-16(3)29)10-11-28(24,9)13-22(35-18(5)31)23(14)27(25,7)8/h20-22,24-26H,2,10-13H2,1,3-9H3/t20-,21-,22-,24-,25-,26-,28-/m0/s1
SMILES	CC(=O)O[C@H]1CC[C@@]2([C@@H](C1=C)[C@H](OC(=O)C)[C@@H]1[C@@H](OC(=O)C)CC(=C([C@H](C2)OC(=O)C)C1(C)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.27	Volume:	521.678 ? Van der Waals volume.
Dense:	0.967	LogP:	2.839 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.919 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.164 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	22.0
TPSA:	105.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.314	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.683	Fsp³:	0.714
MCE-18:	70.0 ? 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:	0.446	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.013 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.385	Promiscuous compounds:	0.616

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.044	MDCK Permeability:	-4.759
Pgp-inhibitor:	1.0	Pgp-substrate:	0.815
PAMPA:	0.16 ? 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):	0.053
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.995
Plasma Protein Binding (PPB):	84.836%	Volume Distribution (VD):	-0.361
Fu:	11.514% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.221
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.05	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.448
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.867	CYP3A4-substrate:	0.42
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.994 ? 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):

5.863

Half-life (T1/2):

0.474

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.047
Human Hepatotoxicity (H-HT):	0.468	Drug-induced Liver Injury (DILI):	0.921
AMES Toxicity:	0.849	Rat Oral Acute Toxicity:	0.29
Maximum Recommended Daily Dose:	0.333	Skin Sensitization:	0.994
Carcinogencity:	0.741	Eye Corrosion:	0.013
Eye Irritation:	0.326	Respiratory Toxicity:	0.083
Drug-induced Neurotoxicity:	0.144	Ototoxicity:	0.375
Hematotoxicity:	0.835	Drug-induced Nephrotoxicity:	0.857
Genotoxicity:	0.927	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.426	Hek293 Cytotoxicity:	0.167
BCF:	0.646 ? 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:	3.674 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.645 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.98 ? 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
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.plantsci.2006.08.002]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(01)00432-0]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	n.a.	n.a.	PMID[12444707]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	Yunnang Province, China	2000-OCT	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21138310]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31343	Taxus chinensis	Species	Taxaceae	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
Activity	9
IC50	2

Activity Type	# Activity
Cell line	2
Individual protein	3
Others	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	130.0	%	PMID[17490878]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	141.0	%	PMID[17490878]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	127.0	%	PMID[17490878]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1475	Cell line	WI-38 VA13	Homo sapiens	IC50	=	53100.0	nM	PMID[17490878]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	18500.0	nM	PMID[17490878]
NPT2	Others	Unspecified	n.a.	Activity	=	105.0	%	PMID[14738387]
NPT2	Others	Unspecified	n.a.	Activity	=	155.0	%	PMID[14738387]
NPT2	Others	Unspecified	n.a.	Activity	=	244.0	%	PMID[14738387]
NPT2	Others	Unspecified	n.a.	Activity	=	91.0	%	PMID[14738387]
NPT2	Others	Unspecified	n.a.	Activity	=	97.0	%	PMID[14738387]
NPT2	Others	Unspecified	n.a.	Activity	=	78.0	%	PMID[14738387]

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 NPC102996 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	26346
0.1-0.2	22186
0.2-0.3	1295
0.3-0.4	16
0.4-0.5	4
0.5-0.6	2
0.6-0.7	4
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC102640
0.9167	High Similarity	NPC479179
0.8627	High Similarity	NPC69713
0.8148	Intermediate Similarity	NPC471786
0.8148	Intermediate Similarity	NPC37603
0.6491	Remote Similarity	NPC220216
0.614	Remote Similarity	NPC261320
0.6	Remote Similarity	NPC124374
0.6	Remote Similarity	NPC479177
0.5714	Remote Similarity	NPC99653
0.5556	Remote Similarity	NPC479171

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC102996 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7758
0.1-0.2	1374
0.2-0.3	18
0.3-0.4	0
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