NPASS Compound

Natural Product: NPC288833

Natural Product ID	NPC288833
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Alpha-Hydroxyolean-12-En-23,29-Dioic Acid
IUPAC Name	(2R,4aS,6aR,6aS,6bR,8aR,9S,10R,12aR,14bR)-10-hydroxy-2,4a,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,9-dicarboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1078928
PubChem CID	44254696
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 81 85 0 0 0 0 0 0 0 0999 V2000 -3.4498 0.3957 2.5183 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5953 0.6496 1.0100 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0620 0.8984 0.8189 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5986 0.7780 -0.5450 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0212 -0.3643 -1.3444 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6572 -1.6854 -1.0091 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5460 -0.4886 -1.1985 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0634 -0.4891 0.2333 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5757 -0.5393 0.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0258 -1.7452 0.0038 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4308 -2.0140 -0.0950 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2440 -0.7464 -0.0638 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7087 -0.9580 0.1233 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1149 -1.7294 1.3303 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1851 -1.7723 -1.0851 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6648 -1.9252 -1.1396 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4702 -0.7170 -0.8868 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8243 0.4286 -0.1728 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4952 0.6862 1.1926 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3709 0.3754 -0.0071 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9121 1.2231 1.1779 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4328 1.4586 1.1157 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6011 0.2388 0.8886 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2683 -0.3949 2.2099 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6982 0.6641 0.2269 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4562 1.1690 -1.1841 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3426 1.7780 0.9924 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8204 1.8995 0.6890 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1752 1.6536 -0.9402 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2531 2.3355 -1.4264 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4783 2.0686 -1.1378 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1081 -0.3086 -2.0871 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3193 -0.0826 -2.7787 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4385 0.0528 -3.6545 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6695 0.0337 -3.1483 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9720 -0.5955 2.6268 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4012 0.3757 3.0421 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8284 1.1793 2.9988 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6196 0.1745 1.4789 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2976 1.9061 1.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6982 0.5897 -0.4800 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4956 1.7472 -1.0761 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5576 -1.9074 0.0849 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0590 -2.4702 -1.5368 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6928 -1.7866 -1.3491 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0681 0.3077 -1.8027 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2307 -1.4551 -1.6510 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4346 -1.4317 0.6892 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6716 -2.6244 -0.0580 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7051 -2.7619 0.6611 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5705 -2.5383 -1.0879 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1294 -0.2853 -1.0841 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1016 -1.1952 2.2785 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2022 -2.0043 1.1733 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6050 -2.7004 1.3389 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7156 -2.7600 -1.0360 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8583 -1.2723 -2.0289 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9997 -2.8075 -0.5120 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8797 -2.3090 -2.1863 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3485 -1.0289 -0.2429 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3525 1.7538 1.4570 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1313 0.0456 1.9828 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5968 0.5772 1.0011 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8945 0.8729 -0.9049 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4145 2.2177 1.0299 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2590 0.8316 2.1353 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1572 1.8998 2.1235 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2533 2.2893 0.4113 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1504 -1.4984 2.1552 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6475 -0.0195 2.6948 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0825 -0.1233 2.9498 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2319 1.9401 -1.4006 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6490 0.3022 -1.8700 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5104 1.6346 -1.3479 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1353 1.8110 2.0601 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8954 2.7372 0.5854 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2050 2.7090 1.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9940 2.2289 -0.3393 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6383 2.9671 -1.5868 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7744 -0.8664 -2.8317 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9439 0.5162 -4.0105 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 1 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 18 29 1 0 29 30 2 0 29 31 1 0 17 32 1 0 5 33 1 0 33 34 2 0 33 35 1 0 28 2 1 0 8 2 1 0 25 9 1 0 23 12 1 0 20 13 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 6 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 8 48 1 1 10 49 1 0 11 50 1 0 11 51 1 0 12 52 1 6 14 53 1 0 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 1 19 61 1 0 19 62 1 0 19 63 1 0 20 64 1 6 21 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 24 69 1 0 24 70 1 0 24 71 1 0 26 72 1 0 26 73 1 0 26 74 1 0 27 75 1 0 27 76 1 0 28 77 1 0 28 78 1 0 31 79 1 0 32 80 1 0 35 81 1 0 M END

Standard InCHIKey	ZZWXYBPRSDQAJH-PPASWHMCSA-N
Standard InCHI	InChI=1S/C30H46O5/c1-25-13-14-26(2,23(32)33)17-19(25)18-7-8-20-27(3)11-10-22(31)30(6,24(34)35)21(27)9-12-29(20,5)28(18,4)16-15-25/h7,19-22,31H,8-17H2,1-6H3,(H,32,33)(H,34,35)/t19-,20+,21+,22+,25+,26+,27+,28+,29+,30-/m0/s1
SMILES	C[C@@]12CC[C@](C)(C[C@H]2C2=CC[C@@H]3[C@@]4(C)CC[C@H]([C@](C)([C@@H]4CC[C@@]3(C)[C@]2(C)CC1)C(=O)O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	520.695 ? Van der Waals volume.
Dense:	0.934	LogP:	3.192 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.734 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.419 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
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:	0.398	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.871	Fsp³:	0.867
MCE-18:	108.571 ? 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:	0.831	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.106 ? 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:	0.419	Promiscuous compounds:	0.071

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.559	MDCK Permeability:	-5.127
Pgp-inhibitor:	0.0	Pgp-substrate:	0.151
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):	0.0
20% Bioavailability (F20%):	0.374	30% Bioavailability (F30%):	0.01
50% Bioavailability (F50%):	0.782

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.999
Plasma Protein Binding (PPB):	94.891%	Volume Distribution (VD):	-0.639
Fu:	4.961% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.0	BCRP inhibitor:	0.006
BSEP inhibitor:	0.972

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.711	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

0.773

Half-life (T1/2):

1.609

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.627	Drug-induced Liver Injury (DILI):	0.604
AMES Toxicity:	0.078	Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.174	Skin Sensitization:	0.997
Carcinogencity:	0.902	Eye Corrosion:	0.622
Eye Irritation:	0.785	Respiratory Toxicity:	0.811
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.562
Hematotoxicity:	0.566	Drug-induced Nephrotoxicity:	0.991
Genotoxicity:	0.842	RPMI-8226 Immunitoxicity:	0.024
A549 Cytotoxicity:	0.016	Hek293 Cytotoxicity:	0.014
BCF:	0.673 ? 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:	3.685 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.229 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.438 ? 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
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19618898]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	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	2

Activity Type	# Activity
Cell line	1
Non-molecular	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
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	62440.0	nM	PMID[19743809]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	47820.0	nM	PMID[19618898]

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 NPC288833 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	25034
0.1-0.2	21316
0.2-0.3	2689
0.3-0.4	600
0.4-0.5	171
0.5-0.6	23
0.6-0.7	14
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC155120
0.7538	Intermediate Similarity	NPC171203
0.7538	Intermediate Similarity	NPC307426
0.7538	Intermediate Similarity	NPC98442
0.7538	Intermediate Similarity	NPC242468
0.7385	Intermediate Similarity	NPC86372
0.7206	Intermediate Similarity	NPC263393
0.6857	Remote Similarity	NPC46441
0.6714	Remote Similarity	NPC474525
0.662	Remote Similarity	NPC78580
0.6522	Remote Similarity	NPC282616
0.6377	Remote Similarity	NPC260385
0.6377	Remote Similarity	NPC110094
0.6377	Remote Similarity	NPC172361
0.6286	Remote Similarity	NPC263272
0.625	Remote Similarity	NPC474964
0.625	Remote Similarity	NPC132824
0.6164	Remote Similarity	NPC474529
0.6111	Remote Similarity	NPC104545
0.6081	Remote Similarity	NPC174663
0.6061	Remote Similarity	NPC221647
0.5972	Remote Similarity	NPC474537
0.5946	Remote Similarity	NPC476064
0.5833	Remote Similarity	NPC7260
0.5833	Remote Similarity	NPC210037
0.5833	Remote Similarity	NPC120968
0.5833	Remote Similarity	NPC227467
0.5833	Remote Similarity	NPC273621
0.56	Remote Similarity	NPC4036
0.56	Remote Similarity	NPC65120
0.56	Remote Similarity	NPC145067
0.56	Remote Similarity	NPC233455
0.56	Remote Similarity	NPC158030
0.5488	Remote Similarity	NPC476878
0.5342	Remote Similarity	NPC477872
0.5294	Remote Similarity	NPC473938
0.5263	Remote Similarity	NPC148523
0.5227	Remote Similarity	NPC476887
0.5217	Remote Similarity	NPC309780
0.5195	Remote Similarity	NPC281524
0.5161	Remote Similarity	NPC482748
0.5135	Remote Similarity	NPC95246
0.5132	Remote Similarity	NPC23621
0.5106	Remote Similarity	NPC482751

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC288833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6894
0.1-0.2	2207
0.2-0.3	39
0.3-0.4	6
0.4-0.5	3
0.5-0.6	1
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
0.56	Remote Similarity	NPD7515	Phase 2

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