NPASS Compound

Natural Product: NPC53744

Natural Product ID	NPC53744
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Olean-12-En-3Bea,15Alpha,24-Triol
IUPAC Name	(3S,4S,4aR,6aR,6bS,7S,8aR,12aR,14aR,14bR)-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,7-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL489552
PubChem CID	14167260
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 83 87 0 0 0 0 0 0 0 0999 V2000 6.8915 0.0414 -1.0329 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4842 0.1171 -1.1051 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8594 -0.2041 0.2418 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3552 -1.6483 0.5093 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3468 0.6364 1.3527 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3892 1.5127 0.9436 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3683 1.4600 2.1017 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9180 1.1112 1.9220 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5758 0.8822 0.4292 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3815 -0.3361 0.1078 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9858 -0.9907 -1.1776 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5849 -1.5660 -0.9034 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6764 -0.3853 -0.7277 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1345 0.6208 0.2734 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3019 1.8805 -0.0027 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1035 1.5400 -0.2420 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6142 0.3189 -0.3591 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7152 -0.8346 -0.2430 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6509 -1.2869 1.1973 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2278 -1.9365 -1.0925 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4510 -3.0892 -0.8187 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6437 -2.3042 -0.8156 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6024 -1.1839 -0.6147 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0926 0.1891 -0.6112 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7696 1.1479 0.3210 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2199 0.8324 0.5934 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4755 -0.5850 0.9694 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2802 -1.4360 0.7410 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5947 1.6900 1.8155 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1233 1.3227 -0.5289 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6655 -1.2911 -1.7241 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4345 0.1853 -2.1047 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9778 2.1582 -0.2140 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2288 0.8190 -1.5211 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1385 1.0747 -1.5377 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2162 -0.6502 -1.8683 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4574 -2.2074 -0.4422 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6353 -2.1849 1.1372 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3860 -1.6130 0.9466 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8910 0.0014 2.1202 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1489 2.4553 1.0819 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5331 1.3765 3.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5425 2.5677 1.9423 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7225 0.1440 2.4289 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3150 1.9325 2.3283 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0754 -1.0775 0.9169 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6653 -1.8512 -1.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9226 -0.3202 -2.0345 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6016 -2.2662 -0.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3256 -2.0500 -1.8920 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7540 0.2799 1.2838 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3628 2.4866 0.9264 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7568 2.4745 -0.8225 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7852 2.4059 -0.3305 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3510 -1.7027 1.4730 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3477 -2.1627 1.3590 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0113 -0.5159 1.9095 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1177 -1.7655 -2.1773 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8035 -3.5657 -0.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6342 -3.0400 0.0462 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9527 -2.9764 -1.6767 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2242 0.6320 -1.6454 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7897 2.1901 -0.1199 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2664 1.2219 1.3079 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7302 -0.7064 2.0652 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4073 -0.9549 0.4548 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5003 -2.5159 0.8556 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5252 -1.1715 1.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6761 1.5753 1.9663 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0061 1.3620 2.7035 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2947 2.7547 1.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7775 0.5277 -0.9245 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4521 1.6609 -1.3689 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7301 2.1847 -0.2599 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6552 -0.3717 -2.3641 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4002 -2.1167 -2.4497 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6483 -1.5498 -1.3354 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7713 -0.5424 -2.9011 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9690 1.1089 -2.3154 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6325 0.3584 -2.3399 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0138 2.4929 -0.0124 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3593 2.9583 0.3022 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7892 2.2641 -1.2719 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 6 3 4 1 0 3 5 1 0 5 6 1 0 5 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 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 26 30 1 0 23 31 1 6 13 32 1 6 9 33 1 6 10 3 1 0 18 13 1 0 28 23 1 0 14 9 1 0 24 17 1 0 1 34 1 0 2 35 1 0 2 36 1 0 4 37 1 0 4 38 1 0 4 39 1 0 5 40 1 1 6 41 1 0 7 42 1 0 7 43 1 0 8 44 1 0 8 45 1 0 10 46 1 1 11 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 14 51 1 1 15 52 1 0 15 53 1 0 16 54 1 0 19 55 1 0 19 56 1 0 19 57 1 0 20 58 1 6 21 59 1 0 22 60 1 0 22 61 1 0 24 62 1 6 25 63 1 0 25 64 1 0 27 65 1 0 27 66 1 0 28 67 1 0 28 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 32 78 1 0 32 79 1 0 32 80 1 0 33 81 1 0 33 82 1 0 33 83 1 0 M END

Standard InCHIKey	DMUKCLRLPXYUKD-LICRDSFHSA-N
Standard InCHI	InChI=1S/C30H50O3/c1-25(2)14-15-26(3)17-24(33)30(7)19(20(26)16-25)8-9-22-27(4)12-11-23(32)28(5,18-31)21(27)10-13-29(22,30)6/h8,20-24,31-33H,9-18H2,1-7H3/t20-,21+,22+,23-,24-,26+,27-,28+,29+,30-/m0/s1
SMILES	OC[C@@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)[C@@H](O)C[C@@]1([C@H]2CC(CC1)(C)C)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	458.38	Volume:	508.388 ? Van der Waals volume.
Dense:	0.902	LogP:	4.176 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.974 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.798 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	26.0
TPSA:	60.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.415	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.994	Fsp³:	0.933
MCE-18:	104.897 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.624	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.04 ? 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:	0.473	Promiscuous compounds:	0.114

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.3	MDCK Permeability:	-4.935
Pgp-inhibitor:	0.311	Pgp-substrate:	0.102
PAMPA:	0.97 ? 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%):	0.984	30% Bioavailability (F30%):	0.283
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	1.0	MRP1:	0.941
Plasma Protein Binding (PPB):	94.074%	Volume Distribution (VD):	-0.189
Fu:	5.294% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.841	BCRP inhibitor:	0.617
BSEP inhibitor:	0.974

ADMET: Metabolism

CYP1A2-inhibitor:	0.064	CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.956	CYP2C19-substrate:	0.647
CYP2C9-inhibitor:	0.057	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.079	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.205	CYP3A4-substrate:	0.764
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.695
HLM stability:	0.734 ? 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):

9.985

Half-life (T1/2):

0.679

ADMET: Toxicity

hERG Blockers:	0.052	hERG Blockers (10um):	0.321
Human Hepatotoxicity (H-HT):	0.633	Drug-induced Liver Injury (DILI):	0.222
AMES Toxicity:	0.578	Rat Oral Acute Toxicity:	0.806
Maximum Recommended Daily Dose:	0.613	Skin Sensitization:	0.99
Carcinogencity:	0.988	Eye Corrosion:	0.011
Eye Irritation:	0.613	Respiratory Toxicity:	0.943
Drug-induced Neurotoxicity:	0.208	Ototoxicity:	0.462
Hematotoxicity:	0.724	Drug-induced Nephrotoxicity:	0.882
Genotoxicity:	0.884	RPMI-8226 Immunitoxicity:	0.096
A549 Cytotoxicity:	0.917	Hek293 Cytotoxicity:	0.831
BCF:	2.065 ? 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:	3.916 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.133 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.633 ? 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
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754608]
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	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
NPT1044	Individual protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	38700.0	nM	PMID[21846091]

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 NPC53744 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	29148
0.1-0.2	17352
0.2-0.3	2675
0.3-0.4	531
0.4-0.5	119
0.5-0.6	21
0.6-0.7	8
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
0.8333	Intermediate Similarity	NPC474989
0.7544	Intermediate Similarity	NPC196753
0.6557	Remote Similarity	NPC480924
0.619	Remote Similarity	NPC230295
0.619	Remote Similarity	NPC238992
0.619	Remote Similarity	NPC98386
0.6167	Remote Similarity	NPC290598
0.6167	Remote Similarity	NPC30590
0.6032	Remote Similarity	NPC253807
0.6032	Remote Similarity	NPC158662
0.5873	Remote Similarity	NPC101475
0.5781	Remote Similarity	NPC478657
0.5692	Remote Similarity	NPC253402
0.5692	Remote Similarity	NPC470588
0.5625	Remote Similarity	NPC311078
0.5625	Remote Similarity	NPC237344
0.5625	Remote Similarity	NPC34177
0.5588	Remote Similarity	NPC213412
0.5493	Remote Similarity	NPC480919
0.5303	Remote Similarity	NPC235341
0.5294	Remote Similarity	NPC246708
0.5286	Remote Similarity	NPC270768
0.5286	Remote Similarity	NPC59263
0.5286	Remote Similarity	NPC210106
0.5278	Remote Similarity	NPC263393
0.5211	Remote Similarity	NPC126369
0.5211	Remote Similarity	NPC470589
0.5211	Remote Similarity	NPC111110
0.5125	Remote Similarity	NPC237503
0.507	Remote Similarity	NPC488519
0.5065	Remote Similarity	NPC480920

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC53744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8314
0.1-0.2	811
0.2-0.3	21
0.3-0.4	3
0.4-0.5	0
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
0.5507	Remote Similarity	NPD7645	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