NPASS Compound

Natural Product: NPC235971

Natural Product ID	NPC235971
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PIMHETLTQXNYHC-NQYXSTDPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21576498
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

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 69 74 0 0 0 0 0 0 0 0999 V2000 -4.4443 -1.1862 -1.5320 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 -1.8532 -0.5316 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8561 -3.3065 -0.5201 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1134 -1.5171 -0.9055 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3050 -2.4902 -1.6590 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0060 -1.8106 -1.8507 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4237 -1.6235 -2.9422 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7161 -1.4028 -0.6151 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1561 -2.6900 0.0408 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2133 -0.5638 0.2609 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5326 -0.1044 1.4533 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5024 0.9649 0.9976 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0615 0.7440 -0.3488 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5248 1.7983 -1.3093 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5702 1.0355 -0.2475 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9172 2.0735 0.6981 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7136 3.4434 0.6104 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 3.9717 1.7689 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7319 2.9835 2.5123 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5622 1.8502 1.9179 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9574 1.3192 -1.5838 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6136 0.3279 -2.5008 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0114 0.4577 -3.6871 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8078 -0.8339 -2.0848 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9256 -0.6095 -0.9531 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2049 -1.4137 -0.8825 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5382 -1.1449 0.4690 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5062 -2.4060 1.3533 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6569 -0.3727 0.9750 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0892 0.9356 0.5613 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1955 2.0992 0.6911 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6480 2.6717 -0.2841 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8860 2.6647 1.9467 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0278 3.7847 2.0675 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7385 -1.2718 0.7144 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8990 -0.5292 -2.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2227 -0.5995 -1.0480 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9321 -1.9514 -2.1904 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3997 -3.5248 0.4459 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0394 -4.0142 -0.5917 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5851 -3.5837 -1.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0944 -0.5645 -1.4904 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7943 -2.6563 -2.6342 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1872 -3.4918 -1.2037 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2654 -2.8559 -0.1377 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7173 -3.6042 -0.4297 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0436 -2.7588 1.1087 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3822 0.3519 -0.3826 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1177 -0.8672 1.9793 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1811 0.3130 2.2082 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9229 1.9271 1.0249 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2689 1.0788 1.7909 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8881 1.4005 -2.0974 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0349 2.6310 -0.7361 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3534 2.3339 -1.8568 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0384 0.0679 0.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2372 3.9623 -0.2096 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2510 5.0225 2.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8772 0.8921 2.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6788 -1.6070 -2.8702 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9450 -2.1521 2.2529 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5585 -2.5995 1.7315 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2496 -3.3106 0.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6122 -0.3848 2.1072 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9772 1.2001 1.2334 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5713 1.0112 -0.4469 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4148 3.9060 1.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4079 3.7518 2.9804 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7127 4.6805 2.0806 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 15 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 25 26 1 1 10 27 1 0 27 28 1 1 27 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 29 35 1 0 35 2 1 0 27 4 1 0 25 8 1 0 25 13 1 0 20 16 2 0 26 24 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 4 42 1 6 5 43 1 0 5 44 1 0 9 45 1 0 9 46 1 0 9 47 1 0 10 48 1 6 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 14 53 1 0 14 54 1 0 14 55 1 0 15 56 1 1 17 57 1 0 18 58 1 0 20 59 1 0 24 60 1 6 28 61 1 0 28 62 1 0 28 63 1 0 29 64 1 1 30 65 1 0 30 66 1 0 34 67 1 0 34 68 1 0 34 69 1 0 M END

Standard InCHIKey	PIMHETLTQXNYHC-NQYXSTDPSA-N
Standard InCHI	InChI=1S/C27H34O8/c1-23(2)16-11-17(28)26(5)15(25(16,4)18(34-23)12-19(29)31-6)7-9-24(3)20(14-8-10-32-13-14)33-22(30)21-27(24,26)35-21/h8,10,13,15-16,18,20-21H,7,9,11-12H2,1-6H3/t15-,16+,18-,20+,21-,24+,25-,26+,27-/m1/s1
SMILES	CC1(C)[C@@H]2CC(=O)[C@]3(C)[C@H](CC[C@@]4(C)[C@H](c5ccoc5)OC(=O)[C@@H]5[C@]34O5)[C@@]2(C)[C@@H](CC(=O)OC)O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.23	Volume:	481.349 ? Van der Waals volume.
Dense:	1.01	LogP:	1.382 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.687 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.431 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	30.0
TPSA:	104.57 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.47	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.667	Fsp³:	0.741
MCE-18:	191.234 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.36	Fluc inhibitor:	0.018 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.008 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.168	Promiscuous compounds:	0.061

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.207	MDCK Permeability:	-4.944
Pgp-inhibitor:	0.895	Pgp-substrate:	0.046
PAMPA:	0.683 ? 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):	0.007
20% Bioavailability (F20%):	0.16	30% Bioavailability (F30%):	0.133
50% Bioavailability (F50%):	0.647

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041	MRP1:	0.98
Plasma Protein Binding (PPB):	87.585%	Volume Distribution (VD):	0.138
Fu:	10.21% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.978
OATP1B3 inhibitor:	0.926	BCRP inhibitor:	0.092
BSEP inhibitor:	0.977

ADMET: Metabolism

CYP1A2-inhibitor:	0.01	CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.981	CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.4	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	0.842
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.41
HLM stability:	0.913 ? 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):

8.772

Half-life (T1/2):

1.174

ADMET: Toxicity

hERG Blockers:	0.066	hERG Blockers (10um):	0.4
Human Hepatotoxicity (H-HT):	0.69	Drug-induced Liver Injury (DILI):	0.761
AMES Toxicity:	0.653	Rat Oral Acute Toxicity:	0.92
Maximum Recommended Daily Dose:	0.947	Skin Sensitization:	0.92
Carcinogencity:	0.605	Eye Corrosion:	0.007
Eye Irritation:	0.928	Respiratory Toxicity:	0.712
Drug-induced Neurotoxicity:	0.571	Ototoxicity:	0.565
Hematotoxicity:	0.424	Drug-induced Nephrotoxicity:	0.818
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.237
A549 Cytotoxicity:	0.009	Hek293 Cytotoxicity:	0.039
BCF:	0.845 ? 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:	3.636 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.532 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.949 ? 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
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	fruit	n.a.	PMID[10820058]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16441086]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	Unripe fruit	n.a.	n.a.	PMID[9644064]
NPO23009	Udotea flabellum	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22906	Bouchardatia neurococca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22962	Coussarea hydrangeifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23009	Udotea flabellum	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20117	Leucas lanata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4954	Eleutherococcus divaricatus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22654	Millettia pachycarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22779	Sphagnum magellanicum	Species	Sphagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10669	Cousinia pterocaulos	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22962	Coussarea hydrangeifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29067	Spondias dulcis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3683.1	Pteridium aquilinum subsp. latiusculum	Subspecies	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22204	Tylostylis discolor	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22906	Bouchardatia neurococca	Species	Rutaceae	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

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

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 NPC235971 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	12776
0.1-0.2	35805
0.2-0.3	1047
0.3-0.4	168
0.4-0.5	26
0.5-0.6	21
0.6-0.7	10
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8133	Intermediate Similarity	NPC237155
0.7662	Intermediate Similarity	NPC305016
0.7662	Intermediate Similarity	NPC476861
0.7662	Intermediate Similarity	NPC476850
0.6709	Remote Similarity	NPC470939
0.6623	Remote Similarity	NPC604270
0.6543	Remote Similarity	NPC263265
0.625	Remote Similarity	NPC60973
0.625	Remote Similarity	NPC605384
0.6235	Remote Similarity	NPC476853
0.619	Remote Similarity	NPC472653
0.6136	Remote Similarity	NPC123088
0.6092	Remote Similarity	NPC25255
0.6047	Remote Similarity	NPC476856
0.5862	Remote Similarity	NPC193798
0.5862	Remote Similarity	NPC117986
0.5795	Remote Similarity	NPC604177
0.5618	Remote Similarity	NPC476858
0.5595	Remote Similarity	NPC107646
0.5476	Remote Similarity	NPC602263
0.5349	Remote Similarity	NPC134254
0.5349	Remote Similarity	NPC39986
0.5341	Remote Similarity	NPC475381
0.5341	Remote Similarity	NPC476857
0.5281	Remote Similarity	NPC23387
0.5281	Remote Similarity	NPC126723
0.5227	Remote Similarity	NPC209364
0.5227	Remote Similarity	NPC605015
0.5213	Remote Similarity	NPC472651
0.5172	Remote Similarity	NPC335761
0.5169	Remote Similarity	NPC609366
0.5114	Remote Similarity	NPC302369
0.5114	Remote Similarity	NPC470941
0.5114	Remote Similarity	NPC5079
0.5054	Remote Similarity	NPC159232

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC235971 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3706
0.1-0.2	5420
0.2-0.3	24
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