NPASS Compound

Natural Product: NPC152759

Natural Product ID	NPC152759
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Docosane-1,22-Diol
IUPAC Name	docosane-1,22-diol
Synonyms	1,22-Hexadecanediol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL470773
PubChem CID	347359
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

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 70 69 0 0 0 0 0 0 0 0999 V2000 -0.8568 2.0628 -0.6450 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5331 2.7081 -0.6769 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5055 1.7352 -1.2622 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9095 2.3290 -1.2814 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3953 2.6771 0.0869 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4565 1.5080 1.0156 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3898 0.3980 0.5170 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7748 0.8669 0.3577 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7265 -0.1462 -0.1486 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0631 -1.3480 0.6081 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0355 -2.3542 0.9670 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2951 -2.9273 -0.2301 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2157 -3.5518 -1.0813 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2576 1.7293 -2.0357 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6114 1.1478 -2.2167 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9829 -0.1496 -1.6698 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9573 -0.4488 -0.2357 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7610 0.4134 0.6706 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2338 0.4224 0.3860 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8685 -0.9390 0.4952 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7358 -1.5560 1.8450 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4106 -2.9111 1.8152 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8808 -2.8195 1.4700 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6041 -2.0584 2.3616 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8628 1.2453 0.0671 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5910 2.8483 -0.2682 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4073 3.5972 -1.3622 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7588 3.0076 0.3458 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4410 0.7734 -0.7546 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2906 1.5475 -2.3568 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8398 3.2736 -1.8650 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5577 1.6173 -1.8036 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3827 3.1778 -0.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7246 3.4473 0.5234 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7944 1.8783 2.0045 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4704 1.0621 1.1407 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9945 0.1108 -0.4981 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2183 -0.4350 1.1967 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1621 1.3275 1.3149 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7533 1.7331 -0.3839 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7173 0.3818 -0.3838 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4306 -0.4559 -1.2258 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8824 -1.9154 0.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5524 -1.0464 1.5938 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6719 -3.2530 1.3674 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3762 -2.1244 1.8030 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5994 -3.6941 0.1374 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7028 -2.1649 -0.7574 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1647 -3.2081 -2.0017 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5401 0.9469 -2.4750 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0935 2.6156 -2.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7306 1.0679 -3.3621 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3328 1.9612 -1.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2473 -0.9067 -2.1413 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9552 -0.5361 -2.1617 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9529 -0.6068 0.1485 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3865 -1.5407 -0.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4050 1.4583 0.5756 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6068 0.0982 1.7069 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5011 0.8440 -0.5865 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7131 1.0633 1.1594 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9694 -0.7773 0.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5364 -1.6545 -0.2604 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6940 -1.7271 2.1625 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1878 -0.9121 2.6532 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9347 -3.4609 0.9505 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2184 -3.5116 2.7041 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2776 -3.8632 1.5469 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0254 -2.5140 0.4176 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2703 -1.1476 2.4854 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 1 0 6 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 1 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 1 25 1 0 1 26 1 0 2 27 1 0 2 28 1 0 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 5 33 1 0 5 34 1 0 6 35 1 0 6 36 1 0 7 37 1 0 7 38 1 0 8 39 1 0 8 40 1 0 9 41 1 0 9 42 1 0 10 43 1 0 10 44 1 0 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 0 14 50 1 0 14 51 1 0 15 52 1 0 15 53 1 0 16 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 24 70 1 0 M END

Standard InCHIKey	HIBKFQRBONXURO-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C22H46O2/c23-21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20-22-24/h23-24H,1-22H2
SMILES	C(CCCCCCCCCCCO)CCCCCCCCCCO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	342.35	Volume:	406.649 ? Van der Waals volume.
Dense:	0.842	LogP:	7.104 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.006 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.584 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	21.0	Rigid Bonds:	0.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.226	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.224	Fsp³:	1.0
MCE-18:	0.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.374	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.98	Promiscuous compounds:	0.547

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.111	MDCK Permeability:	-4.838
Pgp-inhibitor:	0.002	Pgp-substrate:	0.277
PAMPA:	0.001 ? 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):	0.998
20% Bioavailability (F20%):	0.984	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025	MRP1:	0.958
Plasma Protein Binding (PPB):	97.719%	Volume Distribution (VD):	0.872
Fu:	2.691% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.042
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.955
BSEP inhibitor:	0.135

ADMET: Metabolism

CYP1A2-inhibitor:	0.999	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.543	CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.848	CYP2C9-substrate:	0.125
CYP2D6-inhibitor:	0.938	CYP2D6-substrate:	0.336
CYP3A4-inhibitor:	0.01	CYP3A4-substrate:	0.12
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.945
HLM stability:	0.894 ? 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):

5.176

Half-life (T1/2):

1.394

ADMET: Toxicity

hERG Blockers:	0.43	hERG Blockers (10um):	0.74
Human Hepatotoxicity (H-HT):	0.572	Drug-induced Liver Injury (DILI):	0.089
AMES Toxicity:	0.031	Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.095	Skin Sensitization:	0.992
Carcinogencity:	0.33	Eye Corrosion:	0.954
Eye Irritation:	0.998	Respiratory Toxicity:	0.943
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.239
Hematotoxicity:	0.124	Drug-induced Nephrotoxicity:	0.183
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.025
A549 Cytotoxicity:	0.51	Hek293 Cytotoxicity:	0.111
BCF:	1.583 ? 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:	4.784 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.154 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.048 ? 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
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	root bark	n.a.	n.a.	PMID[10346965]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	root	n.a.	PMID[10617409]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473446]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575966]
NPO59816	Mauritia flexuosa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235663]
NPO59816	Mauritia flexuosa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37371565]
NPO59816	Mauritia flexuosa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38945600]
NPO59816	Mauritia flexuosa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39561950]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14105.2	Panax pseudo-ginseng var. notoginseng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14105.2	Panax pseudo-ginseng var. notoginseng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	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
NPO59816	Mauritia flexuosa	Oil	Fruits	6.80	n.a.	n.a.	%	PMID[39561950]

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
MIC	6

Activity Type	# Activity
Organism	6

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
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	500.0	ug.mL-1	PMID[10395496]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	500.0	ug.mL-1	PMID[10395496]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	500.0	ug.mL-1	PMID[10395496]

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 NPC152759 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	44215
0.1-0.2	5295
0.2-0.3	271
0.3-0.4	39
0.4-0.5	7
0.5-0.6	6
0.6-0.7	2
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC12231
0.9091	High Similarity	NPC213764
0.7857	Intermediate Similarity	NPC126915
0.7857	Intermediate Similarity	NPC205141
0.7857	Intermediate Similarity	NPC24506
0.7857	Intermediate Similarity	NPC225783
0.7857	Intermediate Similarity	NPC279895
0.7857	Intermediate Similarity	NPC185538
0.7857	Intermediate Similarity	NPC181516
0.7857	Intermediate Similarity	NPC163556
0.7857	Intermediate Similarity	NPC139131
0.7857	Intermediate Similarity	NPC236797
0.7857	Intermediate Similarity	NPC291158
0.7857	Intermediate Similarity	NPC272998
0.7857	Intermediate Similarity	NPC112242
0.7857	Intermediate Similarity	NPC185041
0.7857	Intermediate Similarity	NPC147096
0.7143	Intermediate Similarity	NPC275462
0.6471	Remote Similarity	NPC469759
0.6471	Remote Similarity	NPC160261
0.5789	Remote Similarity	NPC252978
0.5714	Remote Similarity	NPC52403
0.55	Remote Similarity	NPC474914
0.55	Remote Similarity	NPC474392
0.55	Remote Similarity	NPC76976
0.5385	Remote Similarity	NPC294703

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC152759 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8482
0.1-0.2	617
0.2-0.3	45
0.3-0.4	2
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	2
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
0.7857	Intermediate Similarity	NPD2272	Phase 4
0.7857	Intermediate Similarity	NPD5383	Phase 4

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