NPASS Compound

Natural Product: NPC162703

Natural Product ID	NPC162703
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YKBGDHRTEYNXDH-PJIGFUFZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	71530780
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 77 80 0 0 0 0 0 0 0 0999 V2000 3.4016 -2.6043 0.8723 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2049 -1.7776 -0.3467 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2095 -0.7166 -0.6139 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4297 0.3375 0.4024 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5084 1.2312 -0.1706 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6249 1.3579 0.5140 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7690 0.6392 1.7788 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6947 2.2143 -0.0072 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5323 2.8115 -1.0930 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8851 2.3795 0.6744 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8712 -1.5226 -0.8646 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2004 -2.8764 -1.2652 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2604 -2.5410 -1.3895 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3509 -1.0507 -1.1141 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0144 -0.3128 -2.3652 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6523 -0.6379 -0.6161 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7315 0.4034 0.2056 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4968 1.0757 0.5600 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5815 2.2231 1.0682 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8450 0.4683 0.3479 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7807 -0.9459 -0.0676 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3163 -1.7945 1.0978 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0803 0.7747 0.6830 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4699 -0.3085 1.7012 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1480 2.0748 1.4042 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5744 2.2182 1.9470 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5895 1.9732 0.9163 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7444 2.2632 1.1737 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2819 1.4011 -0.3972 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4407 0.4764 -0.7931 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3202 2.5445 -1.4111 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0181 0.6422 -0.4741 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2180 -0.8552 -0.7177 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8363 -1.3699 -1.0396 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8113 -2.4484 -1.6834 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5204 -2.7243 0.9932 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0678 -2.1295 1.8109 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0285 -3.6444 0.7580 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5766 -2.5978 -1.1597 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9516 -0.1935 -1.5924 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2337 -1.1407 -0.8467 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8155 -0.1815 1.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5822 0.9217 0.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3057 1.7192 -1.1129 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9773 1.0177 2.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7949 -0.4545 1.7019 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7527 0.9477 2.2367 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5869 3.0738 0.4272 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9443 -0.9816 -1.8283 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4439 -3.6460 -0.5253 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6071 -3.1667 -2.2587 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6157 -2.7957 -2.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8605 -3.1387 -0.6422 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6507 0.5394 -2.2488 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9733 0.0831 -2.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3909 -1.0015 -3.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4501 1.1082 -0.3371 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3442 0.6083 1.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7682 -2.0301 1.0579 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4218 -1.1893 2.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8404 -2.7614 1.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5434 -0.3266 1.8949 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0062 -1.2702 1.4653 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9899 0.0234 2.6687 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9540 2.9640 0.8099 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5226 1.9810 2.3224 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6670 3.2539 2.3531 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7359 1.5144 2.7814 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4458 -0.4487 -0.2077 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4206 0.3019 -1.9010 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3834 1.0421 -0.5975 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3594 3.0906 -1.4304 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1718 3.2001 -1.1053 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5913 2.1026 -2.3858 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4603 0.9977 -1.3905 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9081 -1.0186 -1.5471 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5621 -1.3968 0.1602 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 2 0 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 2 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 1 17 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 29 31 1 0 29 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 21 11 1 0 32 23 1 0 21 14 1 0 34 16 1 0 1 36 1 0 1 37 1 0 1 38 1 0 2 39 1 6 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 0 7 45 1 0 7 46 1 0 7 47 1 0 10 48 1 0 11 49 1 6 12 50 1 0 12 51 1 0 13 52 1 0 13 53 1 0 15 54 1 0 15 55 1 0 15 56 1 0 20 57 1 0 20 58 1 0 22 59 1 0 22 60 1 0 22 61 1 0 24 62 1 0 24 63 1 0 24 64 1 0 25 65 1 0 25 66 1 0 26 67 1 0 26 68 1 0 30 69 1 0 30 70 1 0 30 71 1 0 31 72 1 0 31 73 1 0 31 74 1 0 32 75 1 6 33 76 1 0 33 77 1 0 M END

Standard InCHIKey	YKBGDHRTEYNXDH-PJIGFUFZSA-N
Standard InCHI	InChI=1S/C30H42O5/c1-17(9-8-10-18(2)26(34)35)19-11-14-29(6)25-20(31)15-22-27(3,4)23(33)12-13-28(22,5)24(25)21(32)16-30(19,29)7/h10,17,19,22H,8-9,11-16H2,1-7H3,(H,34,35)/b18-10+/t17-,19-,22+,28+,29+,30-/m1/s1
SMILES	C[C@H](CC/C=C(C)/C(=O)O)[C@H]1CC[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	482.3	Volume:	521.343 ? Van der Waals volume.
Dense:	0.925	LogP:	3.625 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.012 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.089 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	25.0
TPSA:	88.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.478	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.747	Fsp³:	0.733
MCE-18:	83.692 ? 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:	0.804	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.02 ? 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:	0.495	Promiscuous compounds:	0.238

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.054	MDCK Permeability:	-4.866
Pgp-inhibitor:	0.814	Pgp-substrate:	0.0
PAMPA:	0.963 ? 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):	0.003
20% Bioavailability (F20%):	0.026	30% Bioavailability (F30%):	0.216
50% Bioavailability (F50%):	0.87

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.983
Plasma Protein Binding (PPB):	81.288%	Volume Distribution (VD):	-0.14
Fu:	18.165% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.988

ADMET: Metabolism

CYP1A2-inhibitor:	0.828	CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.297
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.669
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.996
HLM stability:	0.998 ? 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):

4.596

Half-life (T1/2):

0.631

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.015
Human Hepatotoxicity (H-HT):	0.92	Drug-induced Liver Injury (DILI):	0.814
AMES Toxicity:	0.389	Rat Oral Acute Toxicity:	0.337
Maximum Recommended Daily Dose:	0.507	Skin Sensitization:	0.999
Carcinogencity:	0.811	Eye Corrosion:	0.003
Eye Irritation:	0.479	Respiratory Toxicity:	0.5
Drug-induced Neurotoxicity:	0.053	Ototoxicity:	0.691
Hematotoxicity:	0.919	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.114
A549 Cytotoxicity:	0.032	Hek293 Cytotoxicity:	0.19
BCF:	0.651 ? 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:	3.704 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.395 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.493 ? 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
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15095145]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[17932820]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21115251]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517145]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31891260]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[8594142]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	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
IC50	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT270	Individual protein	Nitric oxide synthase, inducible	Mus musculus	IC50	=	5000.0	nM	PMID[23517145]

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 NPC162703 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	26552
0.1-0.2	20752
0.2-0.3	2136
0.3-0.4	291
0.4-0.5	91
0.5-0.6	21
0.6-0.7	9
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
0.8197	Intermediate Similarity	NPC8571
0.7273	Intermediate Similarity	NPC456
0.7273	Intermediate Similarity	NPC472941
0.7273	Intermediate Similarity	NPC202814
0.6875	Remote Similarity	NPC472931
0.6769	Remote Similarity	NPC142253
0.6769	Remote Similarity	NPC3511
0.6389	Remote Similarity	NPC472924
0.6324	Remote Similarity	NPC87552
0.6197	Remote Similarity	NPC489798
0.6111	Remote Similarity	NPC489789
0.6061	Remote Similarity	NPC484799
0.6027	Remote Similarity	NPC604630
0.5915	Remote Similarity	NPC601194
0.5821	Remote Similarity	NPC90965
0.5811	Remote Similarity	NPC478297
0.5797	Remote Similarity	NPC41539
0.5775	Remote Similarity	NPC472239
0.5735	Remote Similarity	NPC605549
0.5588	Remote Similarity	NPC16287
0.5571	Remote Similarity	NPC472940
0.5556	Remote Similarity	NPC607625
0.5301	Remote Similarity	NPC472935
0.5286	Remote Similarity	NPC99909
0.5231	Remote Similarity	NPC473038
0.52	Remote Similarity	NPC483394
0.5195	Remote Similarity	NPC489802
0.5135	Remote Similarity	NPC472930
0.5135	Remote Similarity	NPC489792
0.507	Remote Similarity	NPC209882
0.507	Remote Similarity	NPC607131
0.5065	Remote Similarity	NPC285702
0.5065	Remote Similarity	NPC166745
0.5065	Remote Similarity	NPC235464

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC162703 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6623
0.1-0.2	2413
0.2-0.3	114
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