NPASS Compound

Natural Product: NPC118964

Natural Product ID	NPC118964
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1Beta-Hydroxy-2-Oxopomolic Acid
IUPAC Name	(1R,2R,4aS,6aS,6aS,6bR,8aS,10R,12S,12aR,14bS)-1,10,12-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-11-oxo-3,4,5,6,6a,7,8,8a,10,12,13,14b-dodecahydro-2H-picene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL461068
PubChem CID	10625284
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 82 86 0 0 0 0 0 0 0 0999 V2000 -5.3711 -2.2312 -1.4447 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6267 -1.8109 -0.5701 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1316 -1.8530 -0.6707 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8717 -2.2459 -2.0031 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6927 -0.3846 -0.5485 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2405 0.2840 -1.7623 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1505 0.2155 0.7453 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6075 0.0876 1.0374 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2013 -1.2323 0.6475 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5955 -1.1141 0.5526 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4378 1.2549 0.5472 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7536 0.1555 2.5719 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7065 1.6350 0.7896 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2770 1.8997 0.5616 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5458 0.9391 -0.3187 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1826 -0.3980 -0.4595 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5101 -1.2292 -1.4852 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9419 -1.0499 -1.4287 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5946 -0.1934 -0.6133 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8241 0.6728 0.3362 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5706 -0.0322 1.6241 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5004 1.9872 0.5674 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7177 2.2251 -0.2213 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7282 1.0814 -0.2388 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0840 -0.1755 -0.7229 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6815 -1.4515 -0.2314 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5279 -2.1482 -1.3077 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6162 -2.3571 -0.0053 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4745 -1.3836 1.0076 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7101 -1.6826 2.2832 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2743 -0.1369 1.2119 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3464 1.0347 1.1049 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7550 1.5421 -1.2063 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9162 1.7596 -0.8408 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4106 1.7302 -2.5302 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2147 1.5699 -1.6586 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6606 -2.4955 0.0656 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6128 -2.0154 -2.5979 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2950 -0.1169 -1.8828 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2187 1.3702 -1.7634 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7232 -0.1724 -2.6510 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6191 -0.3341 1.5571 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0345 -1.9832 1.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9088 -1.4782 -0.3027 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5080 0.8977 0.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2262 1.5732 -0.4664 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3777 2.1029 1.2879 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0865 -0.5704 3.0470 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5405 1.2071 2.8832 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7976 -0.1087 2.7838 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9886 2.0371 1.8079 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3684 2.2230 0.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2045 2.9165 0.0660 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7437 2.0789 1.5431 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9957 -0.9305 0.5275 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6880 -2.3148 -1.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9089 -1.0961 -2.5122 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5380 -1.6749 -2.1170 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7142 -1.1255 1.5959 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3699 0.3357 2.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3688 0.1702 2.1246 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7721 2.0603 1.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8046 2.8341 0.3965 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6031 2.5726 -1.2540 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2810 3.0654 0.2908 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2570 -0.1814 -1.8478 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0370 -2.9981 -0.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8447 -2.5967 -2.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2838 -1.4841 -1.7207 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9986 -3.2195 0.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2550 -2.2176 0.9695 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3109 -2.2834 3.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4374 -0.7595 2.8259 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7756 -2.2334 2.0680 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7492 -0.2060 2.2230 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0383 -0.1081 0.4123 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9254 1.9855 1.2300 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6246 1.0450 1.9451 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0797 1.8985 -3.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7701 1.2972 -2.0571 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2128 2.6830 -1.5002 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9381 1.3864 -2.4469 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 3 5 1 0 5 6 1 6 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 8 11 1 0 8 12 1 0 7 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 1 26 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 24 33 1 6 33 34 2 0 33 35 1 0 15 36 1 6 9 2 1 0 20 15 1 0 32 24 1 0 16 5 1 0 25 19 1 0 3 37 1 1 4 38 1 0 6 39 1 0 6 40 1 0 6 41 1 0 7 42 1 1 9 43 1 1 10 44 1 0 11 45 1 0 11 46 1 0 11 47 1 0 12 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 16 55 1 1 17 56 1 0 17 57 1 0 18 58 1 0 21 59 1 0 21 60 1 0 21 61 1 0 22 62 1 0 22 63 1 0 23 64 1 0 23 65 1 0 25 66 1 6 27 67 1 0 27 68 1 0 27 69 1 0 28 70 1 0 29 71 1 6 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 32 77 1 0 32 78 1 0 35 79 1 0 36 80 1 0 36 81 1 0 36 82 1 0 M END

Standard InCHIKey	VBLIMTVKFVIDFU-PAZRJNPVSA-N
Standard InCHI	InChI=1S/C30H46O6/c1-16-10-13-30(24(34)35)15-14-26(4)17(21(30)29(16,7)36)8-9-19-27(26,5)12-11-18-25(2,3)22(32)20(31)23(33)28(18,19)6/h8,16,18-19,21-23,32-33,36H,9-15H2,1-7H3,(H,34,35)/t16-,18+,19+,21-,22+,23-,26-,27-,28+,29-,30+/m1/s1
SMILES	O=C1[C@@H](O)[C@@]2(C)[C@H](C([C@H]1O)(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@H](C)CC1)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	502.33	Volume:	529.486 ? Van der Waals volume.
Dense:	0.949	LogP:	2.313 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.344 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.185 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	28.0
TPSA:	115.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.396	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.315	Fsp³:	0.867
MCE-18:	112.5 ? 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:	0.525	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.085 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.305	Promiscuous compounds:	0.068

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.594	MDCK Permeability:	-5.119
Pgp-inhibitor:	0.003	Pgp-substrate:	0.052
PAMPA:	1.0 ? 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):	0.002
20% Bioavailability (F20%):	0.28	30% Bioavailability (F30%):	0.063
50% Bioavailability (F50%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054	MRP1:	0.991
Plasma Protein Binding (PPB):	82.987%	Volume Distribution (VD):	-0.417
Fu:	13.746% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.946	BCRP inhibitor:	0.003
BSEP inhibitor:	0.872

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.47	CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.049	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.226	CYP3A4-substrate:	0.013
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.032
HLM stability:	0.45 ? 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):

2.302

Half-life (T1/2):

1.629

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.045
Human Hepatotoxicity (H-HT):	0.8	Drug-induced Liver Injury (DILI):	0.777
AMES Toxicity:	0.432	Rat Oral Acute Toxicity:	0.757
Maximum Recommended Daily Dose:	0.646	Skin Sensitization:	0.994
Carcinogencity:	0.908	Eye Corrosion:	0.003
Eye Irritation:	0.357	Respiratory Toxicity:	0.971
Drug-induced Neurotoxicity:	0.193	Ototoxicity:	0.781
Hematotoxicity:	0.682	Drug-induced Nephrotoxicity:	0.976
Genotoxicity:	0.989	RPMI-8226 Immunitoxicity:	0.087
A549 Cytotoxicity:	0.567	Hek293 Cytotoxicity:	0.22
BCF:	0.625 ? 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:	3.472 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.132 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.41 ? 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
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473413]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	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	1
IC50	2

Activity Type	# Activity
Individual protein	1
Organism	1
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5212	Individual protein	Sentrin-specific protease 1	Homo sapiens	Inhibition	=	1.9	%	PMID[35500202]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	32500.0	nM	PMID[11473413]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	40.0	ug.mL-1	PMID[18180356]

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 NPC118964 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	20520
0.1-0.2	25647
0.2-0.3	3134
0.3-0.4	408
0.4-0.5	113
0.5-0.6	6
0.6-0.7	22
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
0.7879	Intermediate Similarity	NPC256247
0.7536	Intermediate Similarity	NPC157113
0.7536	Intermediate Similarity	NPC284865
0.6901	Remote Similarity	NPC62516
0.6857	Remote Similarity	NPC259733
0.6857	Remote Similarity	NPC158371
0.6857	Remote Similarity	NPC207922
0.6857	Remote Similarity	NPC202728
0.6857	Remote Similarity	NPC158059
0.6667	Remote Similarity	NPC54909
0.6667	Remote Similarity	NPC148964
0.662	Remote Similarity	NPC136697
0.6575	Remote Similarity	NPC187933
0.6575	Remote Similarity	NPC147232
0.6528	Remote Similarity	NPC191412
0.6528	Remote Similarity	NPC114159
0.6528	Remote Similarity	NPC247139
0.6528	Remote Similarity	NPC6818
0.6479	Remote Similarity	NPC235053
0.6301	Remote Similarity	NPC35239
0.6301	Remote Similarity	NPC118519
0.6301	Remote Similarity	NPC132824
0.6234	Remote Similarity	NPC233012
0.6026	Remote Similarity	NPC96693
0.6	Remote Similarity	NPC137072
0.5974	Remote Similarity	NPC603658
0.5823	Remote Similarity	NPC327179
0.5802	Remote Similarity	NPC600756
0.5106	Remote Similarity	NPC25491
0.5053	Remote Similarity	NPC482049
0.5053	Remote Similarity	NPC482050

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC118964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6091
0.1-0.2	2989
0.2-0.3	63
0.3-0.4	7
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