NPASS Compound

Natural Product: NPC312900

Natural Product ID	NPC312900
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gardenolic Acid B
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL558118
PubChem CID	45273405
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 81 85 0 0 0 0 0 0 0 0999 V2000 8.2190 -1.7126 0.1055 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7659 -0.7483 1.1322 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5198 -0.4193 1.3579 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4518 -0.9905 0.5977 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7007 -1.8238 -0.3049 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0020 -0.6243 0.8409 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5382 0.4291 -0.0993 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1583 0.9016 0.0118 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9499 2.0156 -1.0227 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6410 1.7049 -1.7102 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0900 1.0400 -0.5735 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9952 0.0323 -0.1452 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0980 -1.0769 -1.1465 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4162 -0.5401 1.1203 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8446 -1.2951 0.8517 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8446 -0.6124 0.0053 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3516 0.3534 -0.9873 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3611 1.3392 -1.4782 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4787 1.6914 -0.5966 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0462 0.6105 0.2522 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2206 -0.5868 0.4341 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9013 -1.5877 -0.5870 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5519 -1.1749 1.8148 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0817 -0.3598 2.8446 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0669 -1.1746 1.9552 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7802 -1.0650 0.6486 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4599 0.1961 -0.1198 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6594 -0.0993 -1.5675 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4300 1.2431 0.2744 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3391 0.9504 1.0846 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3909 2.5365 -0.2035 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5411 -2.2204 -0.0944 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3929 2.0588 0.4582 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9592 -0.0241 -1.4836 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8184 -0.0885 1.9912 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7412 -2.6943 0.3363 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8874 -1.4434 -0.9323 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3278 -1.7909 0.1236 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2546 0.2946 2.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4758 -1.5864 0.7739 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9876 -0.3193 1.9062 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1918 1.3341 0.1041 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0826 1.3987 1.0257 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7845 2.9987 -0.4816 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7958 2.1930 -1.6690 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1929 2.6693 -2.0173 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7374 1.1000 -2.6098 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7566 -1.8573 -0.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3761 -0.7755 -2.1595 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1249 -1.6112 -1.2335 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1722 0.2656 1.8675 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1041 -1.2247 1.6473 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6482 -2.3499 0.4897 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3048 -1.4874 1.8676 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0784 -0.2241 -1.9270 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7951 1.0435 -2.4818 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7983 2.2820 -1.7490 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3346 2.0751 -1.2314 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2038 2.6227 -0.0140 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1879 1.0809 1.2795 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1630 -1.4805 -1.6535 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8298 -2.6588 -0.2981 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2061 -2.2214 1.8961 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7128 0.4927 2.5536 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4243 -2.0812 2.4642 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4251 -0.3151 2.5891 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8809 -1.1048 0.8987 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1201 0.5173 -2.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7567 0.0661 -1.7918 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5388 -1.2079 -1.7480 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7524 3.3390 0.2909 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2548 -2.8917 -0.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1446 1.6595 1.1732 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4614 2.5073 0.9890 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 2.9424 -0.0915 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0527 0.1710 -1.6318 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4387 0.4341 -2.3129 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8777 -1.1516 -1.5473 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6667 -0.5156 3.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6907 1.0019 2.0077 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8224 -0.3754 1.6722 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 2 0 4 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 6 12 14 1 0 14 15 1 0 16 15 1 1 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 27 29 1 0 29 30 2 0 29 31 1 0 26 32 1 0 11 33 1 1 7 34 1 0 2 35 1 0 12 8 1 0 22 16 1 0 17 11 1 0 27 20 1 0 21 16 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 6 40 1 0 6 41 1 0 7 42 1 1 8 43 1 1 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 13 48 1 0 13 49 1 0 13 50 1 0 14 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 17 55 1 6 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 20 60 1 1 22 61 1 0 22 62 1 0 23 63 1 6 24 64 1 0 25 65 1 0 25 66 1 0 26 67 1 1 28 68 1 0 28 69 1 0 28 70 1 0 31 71 1 0 32 72 1 0 33 73 1 0 33 74 1 0 33 75 1 0 34 76 1 0 34 77 1 0 34 78 1 0 35 79 1 0 35 80 1 0 35 81 1 0 M END

Standard InCHIKey	TTYDGCKGPQOMOK-SESPQYOESA-N
Standard InCHI	InChI=1S/C30H46O5/c1-17(2)13-19(31)14-18(3)20-9-10-27(5)21-7-8-22-28(6,25(34)35)23(32)15-24(33)30(22)16-29(21,30)12-11-26(20,27)4/h13,18,20-24,32-33H,7-12,14-16H2,1-6H3,(H,34,35)/t18-,20-,21+,22+,23+,24+,26-,27+,28+,29+,30-/m1/s1
SMILES	CC(=CC(=O)C[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)[C@@H](O)C[C@@H]([C@@]2(C)C(=O)O)O)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	520.695 ? Van der Waals volume.
Dense:	0.934	LogP:	3.066 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.862 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.436 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	25.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.453	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.951	Fsp³:	0.867
MCE-18:	142.071 ? 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:	0.484	Fluc inhibitor:	0.001 ? 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:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.299	Promiscuous compounds:	0.254

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.54	MDCK Permeability:	-5.067
Pgp-inhibitor:	0.0	Pgp-substrate:	0.044
PAMPA:	0.999 ? 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%):	0.018	30% Bioavailability (F30%):	0.034
50% Bioavailability (F50%):	0.936

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035	MRP1:	0.734
Plasma Protein Binding (PPB):	95.09%	Volume Distribution (VD):	-0.341
Fu:	6.905% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.041
BSEP inhibitor:	0.034

ADMET: Metabolism

CYP1A2-inhibitor:	0.015	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.299	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.879
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.008
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):

6.925

Half-life (T1/2):

1.664

ADMET: Toxicity

hERG Blockers:	0.069	hERG Blockers (10um):	0.137
Human Hepatotoxicity (H-HT):	0.625	Drug-induced Liver Injury (DILI):	0.17
AMES Toxicity:	0.167	Rat Oral Acute Toxicity:	0.556
Maximum Recommended Daily Dose:	0.616	Skin Sensitization:	0.838
Carcinogencity:	0.876	Eye Corrosion:	0.001
Eye Irritation:	0.18	Respiratory Toxicity:	0.91
Drug-induced Neurotoxicity:	0.05	Ototoxicity:	0.737
Hematotoxicity:	0.567	Drug-induced Nephrotoxicity:	0.805
Genotoxicity:	0.589	RPMI-8226 Immunitoxicity:	0.065
A549 Cytotoxicity:	0.318	Hek293 Cytotoxicity:	0.137
BCF:	0.919 ? 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:	3.993 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.585 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.749 ? 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
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	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
EC50	2

Activity Type	# Activity
Cell line	2

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
NPT65	Cell line	HepG2	Homo sapiens	EC50	=	66400.0	nM	PMID[19489592]
NPT65	Cell line	HepG2	Homo sapiens	EC50	=	66400.0	nM	PMID[29353722]

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 NPC312900 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	20802
0.1-0.2	25762
0.2-0.3	2990
0.3-0.4	225
0.4-0.5	52
0.5-0.6	12
0.6-0.7	4
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
0.7969	Intermediate Similarity	NPC235046
0.7231	Intermediate Similarity	NPC302111
0.7164	Intermediate Similarity	NPC201763
0.7164	Intermediate Similarity	NPC288906
0.7164	Intermediate Similarity	NPC611460
0.7015	Intermediate Similarity	NPC56962
0.7015	Intermediate Similarity	NPC24705
0.6761	Remote Similarity	NPC263729
0.6338	Remote Similarity	NPC193934
0.6081	Remote Similarity	NPC71706
0.6027	Remote Similarity	NPC271980
0.5946	Remote Similarity	NPC124207
0.5833	Remote Similarity	NPC290969
0.5735	Remote Similarity	NPC606508
0.5616	Remote Similarity	NPC488976
0.5541	Remote Similarity	NPC263135
0.5467	Remote Similarity	NPC603266
0.5395	Remote Similarity	NPC266431
0.5325	Remote Similarity	NPC81256
0.5325	Remote Similarity	NPC486363
0.527	Remote Similarity	NPC486365
0.5205	Remote Similarity	NPC60350
0.52	Remote Similarity	NPC146937

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC312900 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5887
0.1-0.2	3148
0.2-0.3	113
0.3-0.4	2
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