NPASS Compound

Natural Product: NPC166069

Natural Product ID	NPC166069
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OWPWFVVPBYFKBG-RYSDKYHZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 78 84 0 0 0 0 0 0 0 0999 V2000 -7.9592 1.3433 1.5725 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0140 0.3718 0.9503 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6742 -0.8006 1.8315 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9018 -1.7929 1.0278 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8156 -1.2097 0.1891 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1994 0.1320 -0.3339 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7833 0.9671 0.5929 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1592 0.8018 -0.9633 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9618 0.6986 -0.2986 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9248 1.4833 -1.0160 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5082 1.1898 -0.5006 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4813 1.9864 -1.2585 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6396 1.2690 -1.8104 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1223 0.0648 -1.0820 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1248 -0.6895 -0.2780 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3272 -0.6305 1.2097 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7113 -1.0240 1.6364 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7914 -0.7132 0.6484 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1800 -2.0102 -0.0097 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9354 -0.0316 1.3826 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2827 1.3034 1.6690 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4324 1.6052 0.4424 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4100 0.3508 -0.3361 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4550 0.4279 -1.2887 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1561 0.1549 0.6083 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6124 1.3124 0.1902 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8593 1.1328 -0.5536 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5366 2.0611 -1.0811 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1357 -0.2017 -0.5625 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1199 -0.8867 0.1463 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3035 -0.2987 -0.6075 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2342 -0.9762 0.3545 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6511 -0.7666 -0.1318 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5737 -1.2267 0.8440 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6034 -0.7660 -1.9772 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2598 -1.3514 -2.6315 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6539 -2.0603 -0.9289 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7759 -2.6001 0.2680 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4329 2.1928 2.0166 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6566 0.8254 2.2612 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5936 1.7625 0.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4465 -0.0624 0.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1611 -0.4969 2.7615 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6535 -1.2854 2.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4244 -2.5074 1.7579 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9760 -0.0411 -1.1360 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1072 1.1350 0.7330 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9845 1.3627 -2.1140 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0933 2.5602 -0.8016 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5389 1.4518 0.5813 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0491 2.5118 -2.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7633 2.8650 -0.6008 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5033 2.0033 -1.8273 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4792 1.0871 -2.9167 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4551 -0.6561 -1.9001 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1421 -1.8019 -0.5122 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9805 0.3067 1.6814 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6371 -1.4180 1.6431 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7393 -2.1352 1.8588 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 -0.5805 2.6504 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9111 -2.5264 0.6390 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4290 -1.9326 -1.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2923 -2.7242 0.0124 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1337 -0.5793 2.3370 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6478 1.2569 2.5890 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9536 2.1376 1.8251 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8479 2.4220 -0.1822 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4637 1.9668 0.8190 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4209 1.3154 -1.7145 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1768 2.3264 0.3321 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6314 -1.3725 1.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7125 -1.6010 -0.5727 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1637 -0.5418 1.3785 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0179 -2.0459 0.4370 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8182 -1.2991 -1.0750 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5517 -0.6396 -2.4899 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7150 -1.5807 -1.7741 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6838 -2.2813 -0.6735 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 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 20 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 15 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 31 35 1 6 35 36 2 0 5 37 1 6 4 38 1 0 7 2 1 0 33 9 1 0 34 5 1 0 31 11 1 0 23 14 1 0 30 25 1 0 23 18 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 6 3 43 1 0 3 44 1 0 4 45 1 1 6 46 1 6 9 47 1 1 10 48 1 0 10 49 1 0 11 50 1 1 12 51 1 0 12 52 1 0 13 53 1 0 13 54 1 0 14 55 1 6 15 56 1 6 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 19 61 1 0 19 62 1 0 19 63 1 0 20 64 1 1 21 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 24 69 1 0 26 70 1 0 30 71 1 0 30 72 1 0 32 73 1 0 32 74 1 0 33 75 1 6 35 76 1 0 37 77 1 0 38 78 1 0 M END

Standard InCHIKey	OWPWFVVPBYFKBG-RYSDKYHZSA-N
Standard InCHI	InChI=1S/C29H40O9/c1-15-9-23(31)29(34)25(36-15)37-21-11-17-3-4-20-19(27(17,14-30)12-22(21)38-29)5-7-26(2)18(6-8-28(20,26)33)16-10-24(32)35-13-16/h10,14-15,17-23,25,31,33-34H,3-9,11-13H2,1-2H3/t15-,17+,18-,19-,20-,21-,22-,23-,25+,26-,27-,28+,29+/m1/s1
SMILES	C[C@@H]1C[C@H]([C@]2([C@@H](O1)O[C@@H]1C[C@@H]3CC[C@@H]4[C@@H](CC[C@]5(C)[C@H](CC[C@]45O)C4=CC(=O)OC4)[C@]3(C[C@H]1O2)C=O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	532.27	Volume:	521.447 ? Van der Waals volume.
Dense:	1.021	LogP:	1.295 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.852 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.238 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	37.0
TPSA:	131.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	3.0	Rings:	7.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.278	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.619	Fsp³:	0.862
MCE-18:	125.481 ? 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:	0.74	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? 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:	0.175	Promiscuous compounds:	0.446

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.082	MDCK Permeability:	-4.806
Pgp-inhibitor:	0.002	Pgp-substrate:	0.934
PAMPA:	0.99 ? 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):	0.009
20% Bioavailability (F20%):	0.538	30% Bioavailability (F30%):	0.64
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023	MRP1:	0.336
Plasma Protein Binding (PPB):	81.979%	Volume Distribution (VD):	0.088
Fu:	16.301% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.456
BSEP inhibitor:	0.74

ADMET: Metabolism

CYP1A2-inhibitor:	0.059	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.044	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.264	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.988	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.413
HLM stability:	0.338 ? 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):

3.678

Half-life (T1/2):

3.278

ADMET: Toxicity

hERG Blockers:	0.069	hERG Blockers (10um):	0.424
Human Hepatotoxicity (H-HT):	0.828	Drug-induced Liver Injury (DILI):	0.904
AMES Toxicity:	0.995	Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.984	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.989
Drug-induced Neurotoxicity:	0.213	Ototoxicity:	0.765
Hematotoxicity:	0.85	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.948
A549 Cytotoxicity:	0.665	Hek293 Cytotoxicity:	0.995
BCF:	0.589 ? 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:	3.468 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.133 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.347 ? 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
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252914]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19251412]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37375900]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3369	Anemone narcissiflora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2175	Hyperbaena columbica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8349	Uga sinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26375	Viburnum grandifolium	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9165	Asclepias curassavica	Species	Apocynaceae	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 NPC166069 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	14731
0.1-0.2	32664
0.2-0.3	2221
0.3-0.4	77
0.4-0.5	110
0.5-0.6	15
0.6-0.7	13
0.7-0.8	0
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC253456
1.0	High Similarity	NPC159338
0.8831	High Similarity	NPC488161
0.8831	High Similarity	NPC16569
0.8312	Intermediate Similarity	NPC104585
0.8125	Intermediate Similarity	NPC488162
0.8125	Intermediate Similarity	NPC93416
0.8101	Intermediate Similarity	NPC277374
0.8	Intermediate Similarity	NPC42670
0.8	Intermediate Similarity	NPC19124
0.7805	Intermediate Similarity	NPC157817
0.775	Intermediate Similarity	NPC171619
0.747	Intermediate Similarity	NPC91
0.747	Intermediate Similarity	NPC329905
0.7294	Intermediate Similarity	NPC163365
0.7229	Intermediate Similarity	NPC488160
0.7159	Intermediate Similarity	NPC470094
0.7093	Intermediate Similarity	NPC488158
0.7093	Intermediate Similarity	NPC488159
0.7059	Intermediate Similarity	NPC609258
0.6977	Remote Similarity	NPC474466
0.6966	Remote Similarity	NPC480905
0.6966	Remote Similarity	NPC85369
0.6932	Remote Similarity	NPC225385
0.6889	Remote Similarity	NPC473040
0.6848	Remote Similarity	NPC476221
0.6848	Remote Similarity	NPC477709
0.6742	Remote Similarity	NPC488163
0.6477	Remote Similarity	NPC79193
0.6292	Remote Similarity	NPC298783
0.6154	Remote Similarity	NPC475136
0.6154	Remote Similarity	NPC33934
0.6087	Remote Similarity	NPC142756
0.5823	Remote Similarity	NPC196931
0.5604	Remote Similarity	NPC88668
0.5604	Remote Similarity	NPC250556
0.5556	Remote Similarity	NPC469750
0.5556	Remote Similarity	NPC480915
0.5495	Remote Similarity	NPC480914
0.5309	Remote Similarity	NPC268829
0.5309	Remote Similarity	NPC295110
0.5204	Remote Similarity	NPC188234
0.5181	Remote Similarity	NPC222875
0.5181	Remote Similarity	NPC25177
0.5165	Remote Similarity	NPC473852
0.5122	Remote Similarity	NPC187302
0.5109	Remote Similarity	NPC196429
0.506	Remote Similarity	NPC480913

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC166069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6242
0.1-0.2	2818
0.2-0.3	76
0.3-0.4	6
0.4-0.5	6
0.5-0.6	2
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
0.5833	Remote Similarity	NPD7625	Phase 1
0.5604	Remote Similarity	NPD7507	Pre-clinical

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