NPASS Compound

Natural Product: NPC123555

Natural Product ID	NPC123555
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DJEZYUIBCFEXFX-BMTHBCBRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	637444
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives

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 77 81 0 0 0 0 0 0 0 0999 V2000 5.8126 -1.2675 -0.7719 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0983 -0.6192 0.1262 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6573 -0.8096 0.2780 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0529 -1.9075 -0.5159 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6316 -2.0719 0.0477 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8752 -0.8349 -0.3895 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6785 -0.9787 -1.8878 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5061 0.4474 0.0199 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8566 1.5290 -0.8455 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6099 1.3588 -0.7799 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2528 0.3013 -0.3108 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7463 0.3163 -0.3281 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2975 0.8400 0.9933 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7161 1.3259 0.6934 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7260 2.7098 0.1202 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4553 1.3563 2.0241 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3988 0.3995 -0.2939 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8074 -0.9926 -0.2423 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3569 -1.0032 -0.7091 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6668 -2.1245 -0.0122 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1858 -2.1725 -0.1859 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5096 -0.8823 0.2256 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4941 -0.7483 1.7204 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3787 -1.1249 -2.1682 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9440 -0.1892 -2.8824 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8632 -2.2411 -2.8437 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9793 0.5266 0.0562 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5845 1.2724 -1.1315 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4246 1.3639 1.2716 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8982 1.5871 1.2734 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7393 0.3744 1.0659 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0969 -0.2585 2.2670 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2224 2.0851 2.5585 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8727 -1.1428 -0.9007 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3081 -1.9674 -1.4205 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4747 -1.0531 1.3669 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0120 -1.6000 -1.5821 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6027 -2.8323 -0.3385 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1457 -2.9455 -0.3787 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7662 -2.1320 1.1459 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3827 -0.4187 -2.4964 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7726 -2.0559 -2.2129 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3410 -0.6788 -2.2040 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1268 0.6775 1.0610 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2720 1.5148 -1.8561 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1217 2.5184 -0.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2059 2.2048 -1.1631 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0965 1.0581 -1.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6932 1.7063 1.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3228 0.0269 1.7349 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1829 3.3849 0.8167 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2751 2.7134 -0.8964 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7621 3.0592 0.0825 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9193 0.3729 2.2495 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7281 1.5491 2.8563 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1928 2.1848 1.9981 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4524 0.3243 -0.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3182 0.7921 -1.3280 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4065 -1.6301 -0.9025 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8782 -1.3489 0.7886 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9891 -2.1241 1.0480 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0746 -3.0811 -0.4399 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7922 -2.9618 0.4869 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9702 -2.4505 -1.2299 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5023 -0.9108 2.1761 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1602 -1.5493 2.1523 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9546 0.2103 2.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3623 -2.6119 -3.6543 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2901 2.3201 -1.0283 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7038 1.2222 -0.9981 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3841 0.8170 -2.0929 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0710 0.8256 2.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9191 2.3373 1.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1296 2.4283 0.5849 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6925 0.6774 0.5802 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8394 0.3040 2.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9836 2.6981 2.5247 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 4 5 1 0 5 6 1 0 6 7 1 6 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 14 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 1 19 24 1 6 24 25 2 0 24 26 1 0 8 27 1 0 27 28 1 6 27 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 30 33 1 0 31 2 1 0 27 3 1 0 22 6 1 0 22 11 1 0 19 12 1 0 1 34 1 0 1 35 1 0 3 36 1 1 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 7 41 1 0 7 42 1 0 7 43 1 0 8 44 1 1 9 45 1 0 9 46 1 0 10 47 1 0 12 48 1 6 13 49 1 0 13 50 1 0 15 51 1 0 15 52 1 0 15 53 1 0 16 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 18 59 1 0 18 60 1 0 20 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 26 68 1 0 28 69 1 0 28 70 1 0 28 71 1 0 29 72 1 0 29 73 1 0 30 74 1 6 31 75 1 6 32 76 1 0 33 77 1 0 M END

Standard InCHIKey	DJEZYUIBCFEXFX-BMTHBCBRSA-N
Standard InCHI	InChI=1S/C29H44O4/c1-17-18-9-10-28(6)22(26(18,4)16-21(30)23(17)31)8-7-19-20-15-25(2,3)11-13-29(20,24(32)33)14-12-27(19,28)5/h7,18,20-23,30-31H,1,8-16H2,2-6H3,(H,32,33)/t18-,20-,21+,22+,23-,26-,27+,28+,29-/m0/s1
SMILES	C=C1[C@@H]2CC[C@]3(C)[C@H](CC=C4[C@@H]5CC(C)(C)CC[C@@]5(CC[C@@]34C)C(=O)O)[C@@]2(C)C[C@H]([C@H]1O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.32	Volume:	494.609 ? Van der Waals volume.
Dense:	0.923	LogP:	3.099 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.988 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.764 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	28.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.44	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.987	Fsp³:	0.828
MCE-18:	103.245 ? 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:	0.905	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.387	Promiscuous compounds:	0.076

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.442	MDCK Permeability:	-5.006
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
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):	0.002
20% Bioavailability (F20%):	0.781	30% Bioavailability (F30%):	0.248
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.726	MRP1:	0.64
Plasma Protein Binding (PPB):	92.332%	Volume Distribution (VD):	-0.179
Fu:	8.328% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.964	BCRP inhibitor:	0.03
BSEP inhibitor:	0.368

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.007	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.073	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.27	CYP3A4-substrate:	0.974
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.581
HLM stability:	0.466 ? 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):

3.335

Half-life (T1/2):

1.316

ADMET: Toxicity

hERG Blockers:	0.079	hERG Blockers (10um):	0.11
Human Hepatotoxicity (H-HT):	0.824	Drug-induced Liver Injury (DILI):	0.627
AMES Toxicity:	0.295	Rat Oral Acute Toxicity:	0.466
Maximum Recommended Daily Dose:	0.475	Skin Sensitization:	0.852
Carcinogencity:	0.874	Eye Corrosion:	0.002
Eye Irritation:	0.41	Respiratory Toxicity:	0.903
Drug-induced Neurotoxicity:	0.203	Ototoxicity:	0.708
Hematotoxicity:	0.615	Drug-induced Nephrotoxicity:	0.78
Genotoxicity:	0.633	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.238	Hek293 Cytotoxicity:	0.33
BCF:	1.967 ? 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:	4.479 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.775 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.283 ? 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
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608862]
NPO6706	Arthrobotrys oligospora	Species	Orbiliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21568306]
NPO1425	Salvia palaestina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6677714]
NPO6706	Arthrobotrys oligospora	Species	Orbiliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1425	Salvia palaestina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9258	Plantago cornuti	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4487	Fritillaria thunbergii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6977	Triopha carpenteri	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9258	Plantago cornuti	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4487	Fritillaria thunbergii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5784	Walsura chrysogyne	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1425	Salvia palaestina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9258	Plantago cornuti	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6977	Triopha carpenteri	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9079	Tephrosia egregia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6706	Arthrobotrys oligospora	Species	Orbiliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4487	Fritillaria thunbergii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11435	Tulipa sylvestris	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4873	Plectranthus sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5442	Bryum weigelii	Species	Bryaceae	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 NPC123555 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	22098
0.1-0.2	23398
0.2-0.3	3550
0.3-0.4	486
0.4-0.5	194
0.5-0.6	76
0.6-0.7	29
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
0.7538	Intermediate Similarity	NPC87095
0.75	Intermediate Similarity	NPC84319
0.75	Intermediate Similarity	NPC52021
0.75	Intermediate Similarity	NPC599947
0.7385	Intermediate Similarity	NPC106112
0.7385	Intermediate Similarity	NPC261935
0.7385	Intermediate Similarity	NPC231063
0.7385	Intermediate Similarity	NPC282395
0.7385	Intermediate Similarity	NPC481360
0.7385	Intermediate Similarity	NPC110308
0.7077	Intermediate Similarity	NPC480946
0.7077	Intermediate Similarity	NPC130577
0.7077	Intermediate Similarity	NPC142415
0.7077	Intermediate Similarity	NPC102683
0.6716	Remote Similarity	NPC270768
0.6716	Remote Similarity	NPC59263
0.6716	Remote Similarity	NPC307282
0.6716	Remote Similarity	NPC210106
0.6716	Remote Similarity	NPC282616
0.6716	Remote Similarity	NPC275809
0.6618	Remote Similarity	NPC158141
0.6522	Remote Similarity	NPC298554
0.6471	Remote Similarity	NPC37038
0.6462	Remote Similarity	NPC604575
0.6377	Remote Similarity	NPC472149
0.6377	Remote Similarity	NPC609452
0.6269	Remote Similarity	NPC280654
0.6232	Remote Similarity	NPC64872
0.6232	Remote Similarity	NPC25906
0.6232	Remote Similarity	NPC156981
0.6143	Remote Similarity	NPC271614
0.6143	Remote Similarity	NPC130278
0.6143	Remote Similarity	NPC88116
0.6087	Remote Similarity	NPC474806
0.6087	Remote Similarity	NPC133579
0.6081	Remote Similarity	NPC474727
0.6056	Remote Similarity	NPC291028
0.6056	Remote Similarity	NPC200752
0.6056	Remote Similarity	NPC120840
0.6	Remote Similarity	NPC182797
0.6	Remote Similarity	NPC32118
0.6	Remote Similarity	NPC52169
0.6	Remote Similarity	NPC488562
0.5972	Remote Similarity	NPC201657
0.5972	Remote Similarity	NPC474963
0.5921	Remote Similarity	NPC188833
0.5857	Remote Similarity	NPC198664
0.5833	Remote Similarity	NPC145667
0.5811	Remote Similarity	NPC296164
0.5775	Remote Similarity	NPC121798
0.5775	Remote Similarity	NPC306541
0.5775	Remote Similarity	NPC234346
0.575	Remote Similarity	NPC204407
0.5733	Remote Similarity	NPC96580
0.5694	Remote Similarity	NPC481314
0.5679	Remote Similarity	NPC283849
0.5679	Remote Similarity	NPC28198
0.5679	Remote Similarity	NPC476123
0.5679	Remote Similarity	NPC606107
0.5676	Remote Similarity	NPC481316
0.5616	Remote Similarity	NPC228784
0.5616	Remote Similarity	NPC324341
0.5616	Remote Similarity	NPC601810
0.5542	Remote Similarity	NPC286347
0.5526	Remote Similarity	NPC481315
0.5513	Remote Similarity	NPC481362
0.5479	Remote Similarity	NPC173744
0.5479	Remote Similarity	NPC204961
0.5479	Remote Similarity	NPC73004
0.5479	Remote Similarity	NPC71074
0.5479	Remote Similarity	NPC111214
0.5479	Remote Similarity	NPC37221
0.5479	Remote Similarity	NPC605937
0.5476	Remote Similarity	NPC100383
0.5467	Remote Similarity	NPC25299
0.5467	Remote Similarity	NPC481322
0.5467	Remote Similarity	NPC130520
0.5405	Remote Similarity	NPC259733
0.5405	Remote Similarity	NPC158371
0.5405	Remote Similarity	NPC207922
0.5405	Remote Similarity	NPC32407
0.5405	Remote Similarity	NPC263548
0.5405	Remote Similarity	NPC606320
0.5402	Remote Similarity	NPC171007
0.5402	Remote Similarity	NPC190849
0.5395	Remote Similarity	NPC20235
0.5395	Remote Similarity	NPC299996
0.5395	Remote Similarity	NPC324063
0.5349	Remote Similarity	NPC294112
0.5349	Remote Similarity	NPC284807
0.5333	Remote Similarity	NPC35239
0.5333	Remote Similarity	NPC247139
0.5287	Remote Similarity	NPC266365
0.5287	Remote Similarity	NPC191410
0.5281	Remote Similarity	NPC198621
0.5281	Remote Similarity	NPC216940
0.5263	Remote Similarity	NPC471588
0.5227	Remote Similarity	NPC475472
0.5222	Remote Similarity	NPC605663
0.5205	Remote Similarity	NPC187722
0.5205	Remote Similarity	NPC477289
0.52	Remote Similarity	NPC202728
0.52	Remote Similarity	NPC158059
0.52	Remote Similarity	NPC293564
0.5195	Remote Similarity	NPC222047
0.519	Remote Similarity	NPC601365
0.5172	Remote Similarity	NPC473538
0.5169	Remote Similarity	NPC270667
0.5169	Remote Similarity	NPC164194
0.5135	Remote Similarity	NPC51700
0.5135	Remote Similarity	NPC88716
0.5135	Remote Similarity	NPC68160
0.5135	Remote Similarity	NPC606443
0.5132	Remote Similarity	NPC91010
0.5128	Remote Similarity	NPC479743
0.5068	Remote Similarity	NPC43686
0.5056	Remote Similarity	NPC475611
0.5055	Remote Similarity	NPC136877
0.5055	Remote Similarity	NPC12288

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC123555 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6389
0.1-0.2	2703
0.2-0.3	54
0.3-0.4	3
0.4-0.5	1
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