NPASS Compound

Natural Product: NPC548738

Natural Product ID	NPC548738
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	19882-11-2
IUPAC Name	(1~{R},3~{S},4~{R},7~{R},9~{S},12~{R},13~{R},17~{S},20~{S},21~{R},22~{S})-22-(hydroxymethyl)-3,4,8,8,12,19,19-heptamethyl-23-oxahexacyclo[18.2.1.0^{3,16}.0^{4,13}.0^{7,12}.0^{17,22}]tricos-15-ene-9,21-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 87 0 0 0 0 0 0 0 0999 V2000 -3.8368 2.1352 1.9994 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4355 1.3857 0.8356 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8382 1.9785 0.6290 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6478 1.4942 -0.4185 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0502 0.2708 -0.9853 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5392 0.2762 -0.8991 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8847 0.9028 -1.8599 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5833 1.0359 -1.9815 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2400 0.4318 -0.7893 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7427 0.3647 -0.8786 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2621 -0.5102 -1.9570 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1962 1.7972 -1.1017 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6711 1.8953 -1.0828 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4188 1.0794 -0.1143 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4373 0.3953 -0.8286 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6567 0.1668 0.7653 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3577 -1.1993 0.7244 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8114 0.5871 2.2423 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2191 0.0028 0.5079 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7171 -1.3613 0.8438 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2492 -1.5377 0.7649 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5505 -0.8130 -0.3508 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2939 -1.7738 -1.4883 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7896 -0.3716 0.2070 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5564 0.7246 1.2396 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4761 -1.4974 0.8724 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9764 -1.4440 0.8285 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5034 -0.5542 1.7640 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6749 -0.0425 1.2783 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0110 -0.7919 -0.0130 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6668 -1.9776 0.2262 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5578 -1.0370 -0.4809 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5391 -2.1001 -1.5415 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0059 -3.3176 -1.0737 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9589 2.7097 1.5830 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5032 1.4315 2.7918 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5752 2.8313 2.4101 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2668 1.6497 -0.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4585 1.5680 1.4509 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7682 3.0850 0.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2700 2.0538 -1.1779 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8083 2.2246 -0.2152 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2812 0.2590 -2.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4714 1.3849 -2.6664 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9661 0.7152 -2.9611 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7903 2.1475 -1.9524 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0636 1.1836 0.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5629 -0.5035 -2.8065 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5480 -1.5200 -1.6008 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2043 -0.0733 -2.3539 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8230 2.1083 -2.0990 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6835 2.4455 -0.3599 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0401 1.7541 -2.1460 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8941 3.0018 -0.9328 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0234 1.7769 0.5422 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4634 0.6613 -1.7713 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3851 -0.9733 1.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9304 -1.9265 1.4115 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5487 -1.5438 -0.2938 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1877 1.5124 2.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5186 -0.2208 2.9188 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8595 0.8928 2.3653 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6495 0.7103 1.1867 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0077 -1.5396 1.9242 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2447 -2.1795 0.2970 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7799 -1.3578 1.7593 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0624 -2.6425 0.6013 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3097 -2.6519 -1.2221 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2951 -2.2303 -1.7826 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1505 -1.3375 -2.3792 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3484 0.6106 1.8290 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4009 0.6108 1.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7109 1.7412 0.8255 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1012 -2.4837 0.5679 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2332 -1.4484 1.9824 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3581 -2.4489 1.0883 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 -0.1348 1.9516 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4669 -0.1605 -0.7750 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6584 -2.2790 1.1550 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1495 -1.7353 -2.4125 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5225 -2.2186 -1.9307 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3416 -4.0555 -1.2028 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 16 18 1 0 16 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 1 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 1 6 33 34 1 0 29 2 1 0 32 5 1 0 24 6 1 0 32 27 1 0 22 9 1 0 19 10 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 6 7 44 1 0 8 45 1 0 8 46 1 0 9 47 1 1 11 48 1 0 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 13 53 1 0 13 54 1 0 14 55 1 1 15 56 1 0 17 57 1 0 17 58 1 0 17 59 1 0 18 60 1 0 18 61 1 0 18 62 1 0 19 63 1 1 20 64 1 0 20 65 1 0 21 66 1 0 21 67 1 0 23 68 1 0 23 69 1 0 23 70 1 0 25 71 1 0 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 27 76 1 1 29 77 1 1 30 78 1 6 31 79 1 0 33 80 1 0 33 81 1 0 34 82 1 0 M END

Standard InCHIKey	UHVLMLUQNCPVOJ-AXOVLVJBSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-25(2)14-18-17-8-9-20-27(5)12-11-21(32)26(3,4)19(27)10-13-28(20,6)29(17,7)15-22-30(18,16-31)23(33)24(25)34-22/h8,18-24,31-33H,9-16H2,1-7H3/t18-,19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
SMILES	CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)C[C@H]3O[C@@H]1[C@H](O)[C@]32CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	508.622 ? Van der Waals volume.
Dense:	0.929	LogP:	4.572 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.226 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.197 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	28.0
TPSA:	69.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.465	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.866	Fsp³:	0.933
MCE-18:	118.345 ? 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:	0.62	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? 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:	0.254	Promiscuous compounds:	0.057

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.441	MDCK Permeability:	-4.976
Pgp-inhibitor:	0.193	Pgp-substrate:	0.241
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):	0.019
20% Bioavailability (F20%):	0.854	30% Bioavailability (F30%):	0.199
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.401	MRP1:	0.45
Plasma Protein Binding (PPB):	93.332%	Volume Distribution (VD):	-0.02
Fu:	7.249% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.882	BCRP inhibitor:	0.443
BSEP inhibitor:	0.944

ADMET: Metabolism

CYP1A2-inhibitor:	0.937	CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.992	CYP2C19-substrate:	0.16
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.696	CYP3A4-substrate:	0.949
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.543
HLM stability:	0.515 ? 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):

11.098

Half-life (T1/2):

0.83

ADMET: Toxicity

hERG Blockers:	0.035	hERG Blockers (10um):	0.177
Human Hepatotoxicity (H-HT):	0.436	Drug-induced Liver Injury (DILI):	0.375
AMES Toxicity:	0.803	Rat Oral Acute Toxicity:	0.791
Maximum Recommended Daily Dose:	0.756	Skin Sensitization:	0.97
Carcinogencity:	0.758	Eye Corrosion:	0.01
Eye Irritation:	0.68	Respiratory Toxicity:	0.955
Drug-induced Neurotoxicity:	0.119	Ototoxicity:	0.56
Hematotoxicity:	0.732	Drug-induced Nephrotoxicity:	0.767
Genotoxicity:	0.914	RPMI-8226 Immunitoxicity:	0.13
A549 Cytotoxicity:	0.649	Hek293 Cytotoxicity:	0.375
BCF:	2.098 ? 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:	4.175 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.423 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.916 ? 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
NPO15553	Barringtonia acutangula	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15553	Barringtonia acutangula	Species	Lecythidaceae	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

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

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 NPC548738 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	22740
0.1-0.2	22777
0.2-0.3	3283
0.3-0.4	890
0.4-0.5	112
0.5-0.6	48
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
0.6812	Remote Similarity	NPC294360
0.6301	Remote Similarity	NPC283343
0.6056	Remote Similarity	NPC164349
0.6	Remote Similarity	NPC473160
0.5972	Remote Similarity	NPC480919
0.5921	Remote Similarity	NPC480921
0.5909	Remote Similarity	NPC311078
0.5909	Remote Similarity	NPC101475
0.5821	Remote Similarity	NPC253807
0.5821	Remote Similarity	NPC158662
0.5735	Remote Similarity	NPC159168
0.5692	Remote Similarity	NPC290598
0.5692	Remote Similarity	NPC30590
0.5616	Remote Similarity	NPC49776
0.5616	Remote Similarity	NPC63118
0.5616	Remote Similarity	NPC474436
0.5588	Remote Similarity	NPC235341
0.5584	Remote Similarity	NPC258547
0.5526	Remote Similarity	NPC475263
0.5455	Remote Similarity	NPC88349
0.5455	Remote Similarity	NPC273668
0.5441	Remote Similarity	NPC34177
0.5352	Remote Similarity	NPC246708
0.5316	Remote Similarity	NPC476132
0.5316	Remote Similarity	NPC480920
0.5224	Remote Similarity	NPC27765
0.5224	Remote Similarity	NPC122418
0.5224	Remote Similarity	NPC491014
0.5217	Remote Similarity	NPC237344
0.5217	Remote Similarity	NPC196753
0.5205	Remote Similarity	NPC480946
0.5205	Remote Similarity	NPC130577
0.5205	Remote Similarity	NPC142415
0.5205	Remote Similarity	NPC102683
0.5143	Remote Similarity	NPC40394
0.5143	Remote Similarity	NPC480924
0.5135	Remote Similarity	NPC7260
0.5135	Remote Similarity	NPC182797
0.5135	Remote Similarity	NPC210037
0.5135	Remote Similarity	NPC120968
0.5135	Remote Similarity	NPC171203
0.5135	Remote Similarity	NPC307426
0.5135	Remote Similarity	NPC98442
0.5135	Remote Similarity	NPC488519
0.5135	Remote Similarity	NPC242468
0.5135	Remote Similarity	NPC227467
0.5135	Remote Similarity	NPC273621
0.5135	Remote Similarity	NPC52169
0.5135	Remote Similarity	NPC488562
0.5122	Remote Similarity	NPC474190
0.507	Remote Similarity	NPC238992
0.507	Remote Similarity	NPC470588

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC548738 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7586
0.1-0.2	1531
0.2-0.3	29
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
0.5556	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