NPASS Compound

Natural Product: NPC158344

Natural Product ID	NPC158344
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-Xylopyranosylperiplogenin
IUPAC Name	3-[(3S,5S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-10,13-dimethyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL249248
PubChem CID	44445802
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 79 84 0 0 0 0 0 0 0 0999 V2000 0.1534 0.2786 -2.6334 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1834 0.1492 -1.1197 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9023 1.3973 -0.6425 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3039 1.4309 -1.1666 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0146 0.2505 -0.5377 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3806 -1.0572 -0.8773 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8989 -1.1060 -0.7612 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5640 -1.6816 0.5951 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6533 -1.1311 1.2441 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6749 -0.9576 0.1391 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2140 0.2583 -0.6273 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2204 0.4480 -1.7434 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5516 0.8204 -1.1442 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0593 -0.1547 -0.1345 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9152 -1.1952 -0.8300 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8898 0.6568 0.8711 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5605 0.0593 2.2219 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0400 -0.1035 2.0717 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0233 -0.8121 0.7091 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5029 -2.1154 0.9960 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3238 0.6330 0.5773 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2586 0.1492 1.3714 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5435 0.3029 0.7396 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7005 -0.0243 1.1501 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3580 0.9094 -0.4919 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9726 1.1480 -0.6533 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4272 -2.1025 -1.6551 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3506 0.3402 -0.7348 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1271 0.5863 0.3752 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0137 -0.6296 0.5871 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2699 -0.3855 -0.2411 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0096 0.7536 0.4441 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0225 1.8311 0.8412 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8313 1.7443 0.1710 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5584 0.2308 1.6150 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8323 0.0933 -1.4821 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3518 -0.7886 1.9273 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0425 1.3305 -2.9671 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4955 -0.4369 -3.1317 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2010 -0.0011 -2.9585 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9824 1.3478 0.4792 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3259 2.2939 -0.8826 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7995 2.3430 -0.7228 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3959 1.4864 -2.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8541 0.4091 0.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8065 -1.8697 -0.2525 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6439 -1.3539 -1.9352 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4200 -1.5162 1.2911 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4422 -2.8058 0.5718 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0009 -1.8541 2.0106 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4878 -0.1189 1.6741 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6558 -1.8658 -0.5121 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3611 1.1204 0.0556 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9003 1.3080 -2.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3628 -0.4763 -2.3403 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4594 1.8294 -0.7152 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2803 0.8752 -1.9780 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3919 -2.1799 -0.7291 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9854 -1.0177 -1.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9221 -1.2840 -0.4158 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5503 1.7140 0.9002 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8087 0.7559 3.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9924 -0.9441 2.3303 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6260 -0.7836 2.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5735 0.8804 2.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9308 -2.4884 1.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0900 -0.2856 2.3271 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6366 0.6856 -1.5807 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8260 2.2611 -0.7511 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1143 -2.7792 -1.8349 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5308 0.6812 1.3119 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4761 -1.5322 0.2747 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8698 -1.2951 -0.3150 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8287 1.1215 -0.1777 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9127 1.9052 1.9426 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4997 2.8027 0.5306 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5258 0.3906 1.6948 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4000 0.8274 -1.8231 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5326 -1.7070 2.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 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 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 16 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 7 27 1 6 5 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 11 2 1 0 19 14 1 0 26 21 1 0 34 29 1 0 7 2 1 0 19 10 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 1 6 46 1 0 6 47 1 0 8 48 1 0 8 49 1 0 9 50 1 0 9 51 1 0 10 52 1 6 11 53 1 1 12 54 1 0 12 55 1 0 13 56 1 0 13 57 1 0 15 58 1 0 15 59 1 0 15 60 1 0 16 61 1 1 17 62 1 0 17 63 1 0 18 64 1 0 18 65 1 0 20 66 1 0 22 67 1 0 26 68 1 0 26 69 1 0 27 70 1 0 29 71 1 1 30 72 1 6 31 73 1 6 32 74 1 6 33 75 1 0 33 76 1 0 35 77 1 0 36 78 1 0 37 79 1 0 M END

Standard InCHIKey	PJCAANBWOIEGPP-RWQXGAIOSA-N
Standard InCHI	InChI=1S/C28H42O9/c1-25-7-3-16(37-24-23(32)22(31)20(29)14-36-24)12-27(25,33)9-5-19-18(25)4-8-26(2)17(6-10-28(19,26)34)15-11-21(30)35-13-15/h11,16-20,22-24,29,31-34H,3-10,12-14H2,1-2H3/t16-,17+,18-,19+,20+,22-,23+,24-,25+,26+,27-,28-/m0/s1
SMILES	C[C@@]12CC[C@@H](C[C@]2(CC[C@@H]2[C@@H]1CC[C@]1(C)[C@H](CC[C@]21O)C1=CC(=O)OC1)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	522.28	Volume:	515.344 ? Van der Waals volume.
Dense:	1.013	LogP:	0.761 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.406 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.221 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	32.0
TPSA:	145.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.272	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.153	Fsp³:	0.893
MCE-18:	114.717 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.714	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? 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:	0.138	Promiscuous compounds:	0.423

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.135	MDCK Permeability:	-5.393
Pgp-inhibitor:	0.0	Pgp-substrate:	0.997
PAMPA:	0.997 ? 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):	0.003
20% Bioavailability (F20%):	0.916	30% Bioavailability (F30%):	0.513
50% Bioavailability (F50%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034	MRP1:	0.969
Plasma Protein Binding (PPB):	74.615%	Volume Distribution (VD):	-0.4
Fu:	22.501% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.967
OATP1B3 inhibitor:	0.588	BCRP inhibitor:	0.02
BSEP inhibitor:	0.241

ADMET: Metabolism

CYP1A2-inhibitor:	0.831	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.015	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.853	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.011
HLM stability:	0.102 ? 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):

2.507

Half-life (T1/2):

3.028

ADMET: Toxicity

hERG Blockers:	0.159	hERG Blockers (10um):	0.58
Human Hepatotoxicity (H-HT):	0.805	Drug-induced Liver Injury (DILI):	0.28
AMES Toxicity:	0.702	Rat Oral Acute Toxicity:	0.915
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.844	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.971
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.757
Hematotoxicity:	0.457	Drug-induced Nephrotoxicity:	0.986
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.776
A549 Cytotoxicity:	0.557	Hek293 Cytotoxicity:	0.968
BCF:	0.566 ? 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:	3.08 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.283 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.687 ? 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
NPO587	Saussurea stella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17844995]
NPO587	Saussurea stella	Species	Asteraceae	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	2

Activity Type	# Activity
Cell line	1
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
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	480.0	nM	PMID[10096846]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	230.0	nM	PMID[17844995]

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 NPC158344 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	15073
0.1-0.2	29463
0.2-0.3	4881
0.3-0.4	235
0.4-0.5	81
0.5-0.6	79
0.6-0.7	22
0.7-0.8	1
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8611	High Similarity	NPC219085
0.8219	Intermediate Similarity	NPC99728
0.8219	Intermediate Similarity	NPC87250
0.8219	Intermediate Similarity	NPC244402
0.8219	Intermediate Similarity	NPC50305
0.8108	Intermediate Similarity	NPC84987
0.7349	Intermediate Similarity	NPC608063
0.7308	Intermediate Similarity	NPC157376
0.7308	Intermediate Similarity	NPC142066
0.7308	Intermediate Similarity	NPC603972
0.7143	Intermediate Similarity	NPC474418
0.7089	Intermediate Similarity	NPC17896
0.7089	Intermediate Similarity	NPC469755
0.7089	Intermediate Similarity	NPC284406
0.7089	Intermediate Similarity	NPC197707
0.7089	Intermediate Similarity	NPC251866
0.7059	Intermediate Similarity	NPC475629
0.6941	Remote Similarity	NPC475556
0.6941	Remote Similarity	NPC311706
0.6875	Remote Similarity	NPC34390
0.6707	Remote Similarity	NPC77319
0.6707	Remote Similarity	NPC471351
0.6707	Remote Similarity	NPC471355
0.6386	Remote Similarity	NPC604978
0.6364	Remote Similarity	NPC32793
0.6364	Remote Similarity	NPC116075
0.622	Remote Similarity	NPC99620
0.6164	Remote Similarity	NPC97487
0.6154	Remote Similarity	NPC469749
0.6071	Remote Similarity	NPC6108
0.6071	Remote Similarity	NPC5311
0.6071	Remote Similarity	NPC469750
0.6071	Remote Similarity	NPC77299
0.6071	Remote Similarity	NPC89514
0.6071	Remote Similarity	NPC480906
0.6	Remote Similarity	NPC76572
0.6	Remote Similarity	NPC10823
0.6	Remote Similarity	NPC193382
0.6	Remote Similarity	NPC480914
0.5977	Remote Similarity	NPC471354
0.5977	Remote Similarity	NPC27507
0.5952	Remote Similarity	NPC309034
0.593	Remote Similarity	NPC180079
0.5921	Remote Similarity	NPC72772
0.5914	Remote Similarity	NPC146857
0.5914	Remote Similarity	NPC247190
0.5862	Remote Similarity	NPC9499
0.5862	Remote Similarity	NPC471360
0.5862	Remote Similarity	NPC469751
0.5862	Remote Similarity	NPC471361
0.5862	Remote Similarity	NPC86159
0.5862	Remote Similarity	NPC469752
0.5862	Remote Similarity	NPC469754
0.5862	Remote Similarity	NPC70542
0.5814	Remote Similarity	NPC243196
0.5789	Remote Similarity	NPC10232
0.5778	Remote Similarity	NPC30483
0.5778	Remote Similarity	NPC470897
0.573	Remote Similarity	NPC480907
0.5657	Remote Similarity	NPC194716
0.5591	Remote Similarity	NPC264336
0.5581	Remote Similarity	NPC196429
0.5568	Remote Similarity	NPC146456
0.5543	Remote Similarity	NPC236973
0.5543	Remote Similarity	NPC32177
0.5543	Remote Similarity	NPC469756
0.5543	Remote Similarity	NPC275901
0.5532	Remote Similarity	NPC59288
0.5506	Remote Similarity	NPC471359
0.55	Remote Similarity	NPC329675
0.5484	Remote Similarity	NPC188234
0.5484	Remote Similarity	NPC480910
0.5484	Remote Similarity	NPC240070
0.5484	Remote Similarity	NPC480909
0.5455	Remote Similarity	NPC199428
0.5455	Remote Similarity	NPC109448
0.5455	Remote Similarity	NPC310341
0.5393	Remote Similarity	NPC250556
0.5393	Remote Similarity	NPC83287
0.5376	Remote Similarity	NPC292467
0.5368	Remote Similarity	NPC486143
0.5368	Remote Similarity	NPC486135
0.5368	Remote Similarity	NPC486142
0.5368	Remote Similarity	NPC486137
0.5368	Remote Similarity	NPC486149
0.5341	Remote Similarity	NPC480915
0.5333	Remote Similarity	NPC305574
0.5312	Remote Similarity	NPC232785
0.5312	Remote Similarity	NPC486139
0.5287	Remote Similarity	NPC471633
0.5213	Remote Similarity	NPC27363
0.5208	Remote Similarity	NPC125077
0.52	Remote Similarity	NPC486144
0.52	Remote Similarity	NPC486145
0.52	Remote Similarity	NPC329636
0.52	Remote Similarity	NPC486147
0.52	Remote Similarity	NPC486136
0.52	Remote Similarity	NPC486148
0.5165	Remote Similarity	NPC484202
0.5165	Remote Similarity	NPC93883
0.5111	Remote Similarity	NPC84949
0.5111	Remote Similarity	NPC480562
0.5111	Remote Similarity	NPC74945
0.5111	Remote Similarity	NPC31354
0.5111	Remote Similarity	NPC69576
0.5104	Remote Similarity	NPC610296
0.5102	Remote Similarity	NPC329986
0.5102	Remote Similarity	NPC140092
0.5102	Remote Similarity	NPC486146
0.5063	Remote Similarity	NPC187302
0.5063	Remote Similarity	NPC268829
0.5063	Remote Similarity	NPC295110
0.5056	Remote Similarity	NPC486129
0.5055	Remote Similarity	NPC88668
0.5054	Remote Similarity	NPC72260
0.5051	Remote Similarity	NPC486138
0.5051	Remote Similarity	NPC276838
0.505	Remote Similarity	NPC475590

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158344 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5918
0.1-0.2	3089
0.2-0.3	128
0.3-0.4	2
0.4-0.5	7
0.5-0.6	4
0.6-0.7	0
0.7-0.8	1
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
0.7089	Intermediate Similarity	NPD7319	Approved
0.5393	Remote Similarity	NPD7327	Approved
0.5393	Remote Similarity	NPD7328	Phase 4
0.5393	Remote Similarity	NPD7507	Pre-clinical
0.5054	Remote Similarity	NPD8294	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