NPASS Compound

Natural Product: NPC179412

Natural Product ID	NPC179412
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Antiaroside O
IUPAC Name	(3S,5R,8R,9S,10R,12R,13S,14S,17R)-12,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2419858
PubChem CID	73352255
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides 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 81 86 0 0 0 0 0 0 0 0999 V2000 7.9079 2.4858 0.1636 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8497 1.5624 0.6744 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3466 0.1357 0.6129 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1292 -0.5164 -0.7119 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7128 -0.2863 -1.1554 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9937 0.4683 -0.0576 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6255 1.7191 0.0456 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6905 0.6406 -0.4544 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7541 0.0322 0.4170 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9566 1.1123 1.0262 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4829 0.8705 1.1170 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0748 0.1890 -0.1135 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2766 1.0202 -1.2698 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9062 0.7133 -2.2411 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5782 -1.1525 -0.1579 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2372 -1.9773 1.0630 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2082 -1.9238 1.4395 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0176 -1.3131 0.3518 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5810 0.0920 0.0056 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1823 0.3318 -1.3717 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6678 0.2121 -1.3886 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3265 -0.4836 -0.2831 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5012 -1.2868 -0.8197 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9068 0.4999 0.7265 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2481 -0.4209 1.9015 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0037 -1.2949 1.9087 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4913 -1.4363 0.5223 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7967 -2.7695 0.1237 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0215 1.3091 0.2574 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5965 1.4149 -0.8955 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6933 2.3742 -0.8741 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4461 2.7104 -1.8044 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7533 2.8655 0.4133 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7485 2.2563 1.1808 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0464 -0.3271 -2.6419 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0617 -1.0270 -0.3212 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0617 -1.4767 -1.4722 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2742 -1.9076 -0.5248 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7461 0.2096 0.8049 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5710 2.8657 0.9935 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5153 3.3872 -0.3392 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6116 1.9556 -0.5296 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6917 1.7932 1.7580 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9606 -0.4693 1.4585 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8732 -0.2408 -1.4743 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7563 0.3040 -2.0959 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0429 -0.1139 0.8668 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3950 -0.4390 1.2207 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0790 2.0949 0.4774 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3117 1.3424 2.0599 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2703 0.2696 2.0226 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0657 1.8276 1.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0808 2.0663 -1.2511 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1945 -1.7063 -1.0390 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5694 -3.0220 0.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9156 -1.6606 1.9027 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3081 -1.4781 2.4289 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5590 -2.9836 1.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7588 -1.9104 -0.5800 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8761 0.8446 0.7438 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7822 -0.5188 -2.0011 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8121 1.2407 -1.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0464 1.2787 -1.4111 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4478 -2.3692 -0.5489 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4770 -0.9543 -0.3918 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5436 -1.2923 -1.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1395 1.2151 1.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1366 -1.0171 1.6240 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3966 0.1024 2.8402 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3281 -2.2740 2.3123 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2527 -0.9227 2.6351 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0203 -3.3546 0.1770 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3555 0.8962 -1.8356 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0682 3.0325 1.5331 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1974 1.6350 1.9665 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3012 0.3603 -3.2797 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4754 -2.0463 -0.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2745 -0.9784 -1.4229 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6426 -1.4556 -2.3550 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4124 -2.2235 -0.1699 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1106 -0.7069 0.7335 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 13 14 2 0 12 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 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 24 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 21 35 1 0 15 36 1 0 5 37 1 0 4 38 1 0 3 39 1 0 7 2 1 0 36 9 1 0 19 12 1 0 27 22 1 0 34 29 1 0 27 18 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 1 3 44 1 1 4 45 1 6 5 46 1 6 6 47 1 1 9 48 1 1 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 13 53 1 0 15 54 1 6 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 18 59 1 6 19 60 1 1 20 61 1 0 20 62 1 0 21 63 1 6 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 1 25 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 28 72 1 0 30 73 1 0 34 74 1 0 34 75 1 0 35 76 1 0 36 77 1 0 36 78 1 0 37 79 1 0 38 80 1 0 39 81 1 0 M END

Standard InCHIKey	ZZECMXKPIDHLJI-WIZGEALKSA-N
Standard InCHI	InChI=1S/C29H42O10/c1-14-23(33)24(34)25(35)26(38-14)39-17-5-7-28(13-30)16(10-17)3-4-19-20(28)11-21(31)27(2)18(6-8-29(19,27)36)15-9-22(32)37-12-15/h9,13-14,16-21,23-26,31,33-36H,3-8,10-12H2,1-2H3/t14-,16-,17+,18-,19-,20+,21-,23+,24-,25-,26+,27+,28-,29+/m1/s1
SMILES	C[C@@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1CC[C@@]2(C=O)[C@H](CC[C@@H]3[C@@H]2C[C@H]([C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)O)C1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	550.28	Volume:	538.794 ? Van der Waals volume.
Dense:	1.021	LogP:	0.443 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.179 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.671 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	162.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.19	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.43	Fsp³:	0.862
MCE-18:	114.074 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.746	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? 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:	0.143	Promiscuous compounds:	0.166

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.98	MDCK Permeability:	-5.087
Pgp-inhibitor:	0.0	Pgp-substrate:	0.997
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):	0.004
20% Bioavailability (F20%):	0.125	30% Bioavailability (F30%):	0.151
50% Bioavailability (F50%):	0.906

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.118
Plasma Protein Binding (PPB):	31.519%	Volume Distribution (VD):	-0.555
Fu:	68.397% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.936
OATP1B3 inhibitor:	0.25	BCRP inhibitor:	0.027
BSEP inhibitor:	0.36

ADMET: Metabolism

CYP1A2-inhibitor:	0.073	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.111	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.013
HLM stability:	0.066 ? 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):

1.226

Half-life (T1/2):

5.16

ADMET: Toxicity

hERG Blockers:	0.089	hERG Blockers (10um):	0.49
Human Hepatotoxicity (H-HT):	0.429	Drug-induced Liver Injury (DILI):	0.598
AMES Toxicity:	0.815	Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.792	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.991
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.857
Hematotoxicity:	0.832	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.914
A549 Cytotoxicity:	0.163	Hek293 Cytotoxicity:	0.942
BCF:	0.485 ? 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:	3.184 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.703 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.817 ? 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
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20553004]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	latex	Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Yunnan Province, China	2011-Mar	PMID[24033101]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	trunk bark	Yunnan, China	n.a.	PMID[24582402]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8369	Antiaris toxicaria	Species	Moraceae	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
Inhibition	1

Activity Type	# Activity
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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	82.3	%	PMID[24033101]

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 NPC179412 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	15653
0.1-0.2	28811
0.2-0.3	4825
0.3-0.4	345
0.4-0.5	94
0.5-0.6	73
0.6-0.7	32
0.7-0.8	0
0.8-0.85	2
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	NPC471356
0.8462	Intermediate Similarity	NPC471353
0.8077	Intermediate Similarity	NPC469750
0.7778	Intermediate Similarity	NPC9499
0.7778	Intermediate Similarity	NPC471360
0.7778	Intermediate Similarity	NPC469751
0.7778	Intermediate Similarity	NPC471361
0.7778	Intermediate Similarity	NPC86159
0.7778	Intermediate Similarity	NPC469752
0.7778	Intermediate Similarity	NPC469754
0.7778	Intermediate Similarity	NPC70542
0.7439	Intermediate Similarity	NPC77319
0.7439	Intermediate Similarity	NPC471351
0.7439	Intermediate Similarity	NPC471355
0.7262	Intermediate Similarity	NPC471354
0.7262	Intermediate Similarity	NPC27507
0.716	Intermediate Similarity	NPC99620
0.7108	Intermediate Similarity	NPC480914
0.6905	Remote Similarity	NPC76572
0.6905	Remote Similarity	NPC193382
0.6897	Remote Similarity	NPC173555
0.6889	Remote Similarity	NPC208193
0.6667	Remote Similarity	NPC196429
0.6588	Remote Similarity	NPC480915
0.6484	Remote Similarity	NPC188234
0.6395	Remote Similarity	NPC5311
0.6395	Remote Similarity	NPC17896
0.6395	Remote Similarity	NPC469755
0.6395	Remote Similarity	NPC284406
0.6395	Remote Similarity	NPC197707
0.6395	Remote Similarity	NPC251866
0.6364	Remote Similarity	NPC471359
0.6344	Remote Similarity	NPC125077
0.6304	Remote Similarity	NPC240070
0.6277	Remote Similarity	NPC232785
0.6277	Remote Similarity	NPC486139
0.6263	Remote Similarity	NPC117445
0.6263	Remote Similarity	NPC308262
0.625	Remote Similarity	NPC250556
0.6211	Remote Similarity	NPC329986
0.6211	Remote Similarity	NPC140092
0.6207	Remote Similarity	NPC77299
0.6207	Remote Similarity	NPC480906
0.6163	Remote Similarity	NPC99728
0.6163	Remote Similarity	NPC87250
0.6163	Remote Similarity	NPC244402
0.6163	Remote Similarity	NPC50305
0.6023	Remote Similarity	NPC157376
0.6023	Remote Similarity	NPC142066
0.6023	Remote Similarity	NPC603972
0.5979	Remote Similarity	NPC486138
0.5979	Remote Similarity	NPC276838
0.5977	Remote Similarity	NPC471633
0.5934	Remote Similarity	NPC469753
0.5914	Remote Similarity	NPC30483
0.5914	Remote Similarity	NPC470897
0.587	Remote Similarity	NPC480907
0.5851	Remote Similarity	NPC236973
0.5789	Remote Similarity	NPC471357
0.5789	Remote Similarity	NPC469757
0.5789	Remote Similarity	NPC117702
0.575	Remote Similarity	NPC189588
0.5732	Remote Similarity	NPC196471
0.5699	Remote Similarity	NPC72260
0.5699	Remote Similarity	NPC488162
0.5699	Remote Similarity	NPC93416
0.5684	Remote Similarity	NPC32177
0.5684	Remote Similarity	NPC292467
0.5684	Remote Similarity	NPC469756
0.5684	Remote Similarity	NPC275901
0.567	Remote Similarity	NPC486143
0.567	Remote Similarity	NPC486142
0.567	Remote Similarity	NPC486149
0.5625	Remote Similarity	NPC480910
0.5625	Remote Similarity	NPC480909
0.5604	Remote Similarity	NPC199428
0.5604	Remote Similarity	NPC84949
0.5604	Remote Similarity	NPC109448
0.5604	Remote Similarity	NPC480562
0.5604	Remote Similarity	NPC74945
0.5604	Remote Similarity	NPC310341
0.5604	Remote Similarity	NPC31354
0.5604	Remote Similarity	NPC69576
0.5595	Remote Similarity	NPC475030
0.5577	Remote Similarity	NPC486150
0.551	Remote Similarity	NPC486135
0.551	Remote Similarity	NPC486137
0.5444	Remote Similarity	NPC473852
0.5417	Remote Similarity	NPC488158
0.5417	Remote Similarity	NPC488159
0.54	Remote Similarity	NPC486146
0.5385	Remote Similarity	NPC84987
0.5385	Remote Similarity	NPC309034
0.5361	Remote Similarity	NPC27363
0.534	Remote Similarity	NPC486144
0.534	Remote Similarity	NPC486145
0.534	Remote Similarity	NPC486147
0.534	Remote Similarity	NPC475590
0.534	Remote Similarity	NPC486148
0.5319	Remote Similarity	NPC483822
0.5319	Remote Similarity	NPC305574
0.53	Remote Similarity	NPC469749
0.5238	Remote Similarity	NPC120390
0.5238	Remote Similarity	NPC74259
0.5238	Remote Similarity	NPC475419
0.5238	Remote Similarity	NPC469794
0.5217	Remote Similarity	NPC219085
0.5213	Remote Similarity	NPC83287
0.5192	Remote Similarity	NPC486136
0.5189	Remote Similarity	NPC474908
0.5155	Remote Similarity	NPC474466
0.5152	Remote Similarity	NPC32793
0.5152	Remote Similarity	NPC116075
0.5106	Remote Similarity	NPC480908
0.5104	Remote Similarity	NPC193893
0.51	Remote Similarity	NPC231518
0.51	Remote Similarity	NPC488944
0.5091	Remote Similarity	NPC286809
0.5051	Remote Similarity	NPC40749
0.505	Remote Similarity	NPC55532
0.5047	Remote Similarity	NPC486134
0.5047	Remote Similarity	NPC486141
0.5046	Remote Similarity	NPC474423

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC179412 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6279
0.1-0.2	2775
0.2-0.3	78
0.3-0.4	4
0.4-0.5	2
0.5-0.6	5
0.6-0.7	7
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
0.6897	Remote Similarity	NPD8296	Phase 4
0.6437	Remote Similarity	NPD8335	Phase 4
0.6395	Remote Similarity	NPD7319	Approved
0.6364	Remote Similarity	NPD8380	Approved
0.625	Remote Similarity	NPD7507	Pre-clinical
0.6105	Remote Similarity	NPD8378	Pre-clinical
0.6105	Remote Similarity	NPD8379	Approved
0.5699	Remote Similarity	NPD8294	Phase 4
0.5213	Remote Similarity	NPD7327	Approved
0.5213	Remote Similarity	NPD7328	Phase 4
0.51	Remote Similarity	NPD8033	Approved
0.505	Remote Similarity	NPD8377	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