NPASS Compound

Natural Product: NPC302041

Natural Product ID	NPC302041
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XZEUYTKSAYNYPK-WXPWFURYSA-N
IUPAC Name	n.a.
Synonyms	29-Nor-Cycloartenol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL441883
PubChem CID	14524546
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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 78 82 0 0 0 0 0 0 0 0999 V2000 7.3223 0.4601 -0.4147 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9408 0.5994 1.0344 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8018 1.2041 1.3629 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9280 1.7286 0.3325 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5313 1.2134 0.2537 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3662 -0.2526 -0.0264 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9482 -1.0538 1.0541 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0674 -0.5570 -0.6097 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8974 -2.0587 -0.9210 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4109 -2.3253 -0.9130 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1764 -0.9134 -1.0357 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1429 -0.4841 -2.4446 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6001 -0.8559 -0.6586 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4717 -1.0128 -1.9177 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8810 -1.2946 -1.3658 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3768 0.0608 -0.9111 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7046 -0.1320 -0.2586 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7124 -0.5652 -1.3302 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2599 1.1078 0.3785 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2722 1.9723 1.0492 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9409 2.0852 0.3305 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4445 0.7128 0.0644 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1589 -0.1257 1.2511 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0809 0.2582 0.1781 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0545 1.1700 0.7361 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2964 1.1474 0.0663 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7771 -0.2426 -0.0125 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5105 -0.9511 1.2950 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1901 0.6743 1.3533 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8257 0.0680 2.0791 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3061 -0.0077 -0.5095 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5164 -0.0622 -0.9650 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4133 1.4813 -0.8656 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5517 1.3086 2.4130 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8211 2.8524 0.4715 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3864 1.6416 -0.7010 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9912 1.8555 -0.4647 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0565 1.4572 1.2755 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1079 -0.4111 -0.9243 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4342 -2.0112 1.3113 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9670 -1.3856 0.7798 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0913 -0.4430 1.9945 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0749 -0.0746 -1.6445 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4592 -2.7033 -0.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3098 -2.2603 -1.9539 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0419 -2.8607 -0.0388 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1569 -2.9077 -1.8340 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9303 -1.1328 -2.9353 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3857 0.5869 -2.5591 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7348 -0.6496 -3.1076 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8243 -1.8258 -0.1131 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5651 -0.0817 -2.4822 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2087 -1.9053 -2.4905 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8519 -2.0359 -0.5649 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4865 -1.5923 -2.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4957 0.6848 -1.8189 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6500 -0.9641 0.4700 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7150 -0.4704 -0.8572 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6996 0.1586 -2.1767 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4914 -1.5928 -1.6391 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8707 1.6815 -0.3576 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0365 1.6767 2.1020 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6765 3.0058 1.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3166 2.7370 0.9399 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1129 2.6363 -0.6398 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4367 -1.1985 1.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1123 0.3454 2.2263 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3640 2.2575 0.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8759 0.9676 1.8132 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9470 1.7695 0.6971 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1824 1.6953 -0.8833 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5418 -1.2842 1.4096 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6906 -0.2776 2.1736 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0888 -1.8926 1.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4123 -0.2711 1.2523 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9200 0.7965 2.9144 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3727 -0.8538 2.4866 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8339 -0.0777 1.6551 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 22 21 1 1 22 23 1 0 24 23 1 1 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 19 29 1 0 2 30 1 0 27 8 1 0 27 11 1 0 24 13 1 0 22 16 1 0 24 22 1 0 1 31 1 0 1 32 1 0 1 33 1 0 3 34 1 0 4 35 1 0 4 36 1 0 5 37 1 0 5 38 1 0 6 39 1 6 7 40 1 0 7 41 1 0 7 42 1 0 8 43 1 6 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 12 48 1 0 12 49 1 0 12 50 1 0 13 51 1 1 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 6 17 57 1 1 18 58 1 0 18 59 1 0 18 60 1 0 19 61 1 6 20 62 1 0 20 63 1 0 21 64 1 0 21 65 1 0 23 66 1 0 23 67 1 0 25 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 M END

Standard InCHIKey	XZEUYTKSAYNYPK-WXPWFURYSA-N
Standard InCHI	InChI=1S/C29H48O/c1-19(2)8-7-9-20(3)22-12-14-27(6)25-11-10-23-21(4)24(30)13-15-28(23)18-29(25,28)17-16-26(22,27)5/h8,20-25,30H,7,9-18H2,1-6H3/t20-,21+,22-,23+,24+,25+,26-,27+,28-,29+/m1/s1
SMILES	CC(=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@H](C)[C@H](CC[C@]54C[C@@]35CC[C@]12C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.37	Volume:	473.512 ? Van der Waals volume.
Dense:	0.871	LogP:	5.628 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.218 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.399 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	23.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.467	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.512	Fsp³:	0.931
MCE-18:	123.857 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.922	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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.605	Promiscuous compounds:	0.212

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.825	MDCK Permeability:	-4.948
Pgp-inhibitor:	0.078	Pgp-substrate:	0.039
PAMPA:	0.317 ? 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):	0.001
20% Bioavailability (F20%):	0.062	30% Bioavailability (F30%):	0.383
50% Bioavailability (F50%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.623	MRP1:	0.047
Plasma Protein Binding (PPB):	95.835%	Volume Distribution (VD):	-0.091
Fu:	4.982% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.921
BSEP inhibitor:	0.119

ADMET: Metabolism

CYP1A2-inhibitor:	0.022	CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.018	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.955
HLM stability:	0.77 ? 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):

16.152

Half-life (T1/2):

1.196

ADMET: Toxicity

hERG Blockers:	0.18	hERG Blockers (10um):	0.405
Human Hepatotoxicity (H-HT):	0.464	Drug-induced Liver Injury (DILI):	0.022
AMES Toxicity:	0.221	Rat Oral Acute Toxicity:	0.259
Maximum Recommended Daily Dose:	0.237	Skin Sensitization:	0.9
Carcinogencity:	0.808	Eye Corrosion:	0.064
Eye Irritation:	0.742	Respiratory Toxicity:	0.85
Drug-induced Neurotoxicity:	0.035	Ototoxicity:	0.507
Hematotoxicity:	0.354	Drug-induced Nephrotoxicity:	0.401
Genotoxicity:	0.029	RPMI-8226 Immunitoxicity:	0.058
A549 Cytotoxicity:	0.438	Hek293 Cytotoxicity:	0.189
BCF:	3.294 ? 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:	5.305 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.963 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.397 ? 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
NPO6429	Phlomis regelii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29468889]
NPO6815	Streptomyces sclerotialus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4095	Hedysarum multijugum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4095	Hedysarum multijugum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8037	Bryum rutilans	Species	Bryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4095	Hedysarum multijugum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6815	Streptomyces sclerotialus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6988	Diploschistes cretaceus	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6429	Phlomis regelii	Species	Lamiaceae	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
Inhibition	4
IC50	1
Activity	2

Activity Type	# Activity
Cell line	1
Organism	5
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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[17503850]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[17503850]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	30.2	%	PMID[17503850]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	71.4	%	PMID[17503850]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	94.6	%	PMID[17503850]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	9.5	nM	PMID[17503850]
NPT2	Others	Unspecified	n.a.	Activity	=	1.8	n.a.	PMID[17503850]

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 NPC302041 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	27672
0.1-0.2	19803
0.2-0.3	2078
0.3-0.4	185
0.4-0.5	72
0.5-0.6	39
0.6-0.7	2
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
0.76	Intermediate Similarity	NPC85346
0.76	Intermediate Similarity	NPC65897
0.76	Intermediate Similarity	NPC80237
0.7451	Intermediate Similarity	NPC145552
0.7308	Intermediate Similarity	NPC49168
0.7308	Intermediate Similarity	NPC5046
0.6316	Remote Similarity	NPC89747
0.614	Remote Similarity	NPC230704
0.5965	Remote Similarity	NPC269058
0.5965	Remote Similarity	NPC113978
0.5965	Remote Similarity	NPC71520
0.5893	Remote Similarity	NPC214770
0.5893	Remote Similarity	NPC477856
0.5714	Remote Similarity	NPC604180
0.5636	Remote Similarity	NPC607543
0.5593	Remote Similarity	NPC139206
0.5536	Remote Similarity	NPC331618
0.5536	Remote Similarity	NPC257191
0.5536	Remote Similarity	NPC196358
0.55	Remote Similarity	NPC606508
0.5469	Remote Similarity	NPC283733
0.5455	Remote Similarity	NPC41577
0.5439	Remote Similarity	NPC200243
0.5439	Remote Similarity	NPC254509
0.5439	Remote Similarity	NPC82623
0.5385	Remote Similarity	NPC194937
0.5385	Remote Similarity	NPC476038
0.5357	Remote Similarity	NPC299948
0.5357	Remote Similarity	NPC241085
0.5345	Remote Similarity	NPC472342
0.5323	Remote Similarity	NPC158846
0.5323	Remote Similarity	NPC110923
0.5323	Remote Similarity	NPC74296
0.5231	Remote Similarity	NPC102426
0.5231	Remote Similarity	NPC128496
0.5167	Remote Similarity	NPC76518
0.5156	Remote Similarity	NPC195366
0.5156	Remote Similarity	NPC114743
0.5152	Remote Similarity	NPC300179
0.5085	Remote Similarity	NPC240604
0.5085	Remote Similarity	NPC470830
0.5085	Remote Similarity	NPC195530
0.5085	Remote Similarity	NPC69149
0.5085	Remote Similarity	NPC479659
0.5085	Remote Similarity	NPC273366
0.5082	Remote Similarity	NPC12722
0.5082	Remote Similarity	NPC195489

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC302041 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8206
0.1-0.2	895
0.2-0.3	46
0.3-0.4	3
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