NPASS Compound

Natural Product: NPC86182

Natural Product ID	NPC86182
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WRORFDCUNLGVJF-PQWXPXKJSA-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 83 88 0 0 0 0 0 0 0 0999 V2000 7.1546 -2.1477 -1.6947 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0983 -1.1746 -1.1481 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7072 0.1312 -0.8276 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2428 0.8160 0.4078 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0333 -0.2846 1.4572 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9471 -1.1610 0.8787 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3887 -1.8282 -0.2130 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8101 -0.4573 0.5526 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6818 -0.8166 1.2540 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2867 0.4095 2.0912 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7863 0.4550 2.1045 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1984 0.7680 0.7372 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4987 2.2621 0.5090 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2765 0.6666 0.7556 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7705 1.0267 -0.6386 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2522 0.0608 -1.6674 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1240 -0.4066 -1.4984 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8995 -0.0053 -0.3164 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5318 -1.2259 0.3786 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0476 0.7487 -0.6859 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2250 1.2547 -0.6320 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9222 1.1062 -1.9571 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7333 -0.1586 -1.9286 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8315 -0.5242 -0.5040 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2010 -0.8013 0.0063 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3633 -0.6312 -0.5996 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4733 -1.0364 0.2723 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6992 -1.0169 0.0435 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8998 -1.4652 1.4499 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5231 -1.3444 1.3535 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0734 0.5034 0.3326 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1410 1.3592 0.9942 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3867 -0.2510 1.4137 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9214 -0.5595 1.1890 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8631 -1.6488 0.3530 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3934 2.6310 -0.3021 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7387 0.2214 2.6941 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1137 1.7566 0.8985 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6292 1.0462 -1.9044 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0780 -2.1198 -1.0489 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7448 -3.1751 -1.7748 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4882 -1.8517 -2.7065 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4165 -1.0063 -2.0380 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8194 -0.0371 -0.7074 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2480 1.2793 0.2004 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9528 -0.8762 1.5184 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6837 -1.9000 1.6789 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8452 -1.6318 1.9891 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7786 1.3101 1.7341 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6011 0.2763 3.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4909 1.3001 2.7711 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4397 -0.5277 2.4966 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3515 2.6081 1.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3608 2.9000 0.7592 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7857 2.3969 -0.5755 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6438 1.5069 1.4184 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1998 1.9855 -0.8584 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3218 0.6147 -2.6549 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9817 -0.7886 -1.8124 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7551 -0.1746 -2.4156 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1164 -1.5417 -1.5407 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8111 -1.8105 0.9431 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9113 -1.8624 -0.4582 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2889 0.3816 -1.5921 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6675 1.9357 -2.1487 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2827 1.0885 -2.8302 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2428 -0.9618 -2.5649 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7331 -0.0300 -2.3835 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3100 -1.5343 -0.4091 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5285 -0.2482 -1.5992 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0492 -2.3716 1.3692 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0740 -0.7444 2.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1708 1.1034 0.6733 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9985 2.4083 0.6611 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0183 1.3968 2.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8455 -1.2742 1.5815 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4540 0.2324 2.4121 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5346 -0.9206 2.1882 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8748 -2.5211 0.8436 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9959 2.7624 0.5886 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2905 -0.4892 3.2194 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7356 2.6627 0.7768 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6863 1.9709 -1.5924 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 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 6 15 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 24 31 1 0 31 32 1 1 31 33 1 0 33 34 1 0 34 35 1 0 21 36 1 1 5 37 1 0 4 38 1 0 3 39 1 0 7 2 1 0 19 9 1 0 31 21 1 0 18 12 1 0 30 25 1 0 34 14 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 6 3 44 1 1 4 45 1 6 5 46 1 1 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 13 54 1 0 13 55 1 0 14 56 1 1 15 57 1 6 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 22 65 1 0 22 66 1 0 23 67 1 0 23 68 1 0 24 69 1 6 26 70 1 0 30 71 1 0 30 72 1 0 32 73 1 0 32 74 1 0 32 75 1 0 33 76 1 0 33 77 1 0 34 78 1 1 35 79 1 0 36 80 1 0 37 81 1 0 38 82 1 0 39 83 1 0 M END

Standard InCHIKey	WRORFDCUNLGVJF-PQWXPXKJSA-N
Standard InCHI	InChI=1S/C29H44O10/c1-14-22(32)23(33)24(34)25(38-14)39-16-4-7-26(2)21-18(5-8-28(26,35)11-16)29(36)9-6-17(15-10-20(31)37-13-15)27(29,3)12-19(21)30/h10,14,16-19,21-25,30,32-36H,4-9,11-13H2,1-3H3/t14-,16+,17-,18-,19-,21+,22-,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)[C@H]3[C@@H](CC[C@@]2(C1)O)[C@]1(CC[C@H](C2=CC(=O)OC2)[C@@]1(C)C[C@H]3O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.29	Volume:	541.431 ? Van der Waals volume.
Dense:	1.02	LogP:	-0.561 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.464 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.932 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	32.0
TPSA:	166.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.215	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.362	Fsp³:	0.897
MCE-18:	119.127 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.642	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.027 ? 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:	0.114	Promiscuous compounds:	0.436

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.641	MDCK Permeability:	-5.274
Pgp-inhibitor:	0.0	Pgp-substrate:	0.996
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):	0.033
20% Bioavailability (F20%):	0.827	30% Bioavailability (F30%):	0.293
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017	MRP1:	0.957
Plasma Protein Binding (PPB):	66.331%	Volume Distribution (VD):	-0.371
Fu:	33.634% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.963
OATP1B3 inhibitor:	0.724	BCRP inhibitor:	0.008
BSEP inhibitor:	0.084

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.14
HLM stability:	0.014 ? 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):

1.792

Half-life (T1/2):

3.214

ADMET: Toxicity

hERG Blockers:	0.084	hERG Blockers (10um):	0.441
Human Hepatotoxicity (H-HT):	0.673	Drug-induced Liver Injury (DILI):	0.474
AMES Toxicity:	0.933	Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.759	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.99
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.809
Hematotoxicity:	0.761	Drug-induced Nephrotoxicity:	0.988
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.923
A549 Cytotoxicity:	0.99	Hek293 Cytotoxicity:	0.992
BCF:	0.556 ? 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:	3.095 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.388 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.733 ? 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
NPO30971	Cheiranthus cheiri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[39575377]
NPO30971	Cheiranthus cheiri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30971	Cheiranthus cheiri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30971	Cheiranthus cheiri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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 NPC86182 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	15499
0.1-0.2	29201
0.2-0.3	4725
0.3-0.4	245
0.4-0.5	90
0.5-0.6	52
0.6-0.7	27
0.7-0.8	3
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8243	Intermediate Similarity	NPC99728
0.8243	Intermediate Similarity	NPC87250
0.8243	Intermediate Similarity	NPC244402
0.8243	Intermediate Similarity	NPC50305
0.7595	Intermediate Similarity	NPC83287
0.7564	Intermediate Similarity	NPC157376
0.7564	Intermediate Similarity	NPC17896
0.7564	Intermediate Similarity	NPC469755
0.7564	Intermediate Similarity	NPC284406
0.7564	Intermediate Similarity	NPC197707
0.7564	Intermediate Similarity	NPC251866
0.7564	Intermediate Similarity	NPC142066
0.7564	Intermediate Similarity	NPC603972
0.7375	Intermediate Similarity	NPC77319
0.7375	Intermediate Similarity	NPC471351
0.7375	Intermediate Similarity	NPC471355
0.7215	Intermediate Similarity	NPC84987
0.6897	Remote Similarity	NPC264336
0.6818	Remote Similarity	NPC59288
0.679	Remote Similarity	NPC309034
0.675	Remote Similarity	NPC158344
0.6667	Remote Similarity	NPC9499
0.6667	Remote Similarity	NPC99620
0.6667	Remote Similarity	NPC471360
0.6667	Remote Similarity	NPC469751
0.6667	Remote Similarity	NPC471361
0.6667	Remote Similarity	NPC86159
0.6667	Remote Similarity	NPC469752
0.6667	Remote Similarity	NPC469754
0.6667	Remote Similarity	NPC70542
0.6588	Remote Similarity	NPC471354
0.6588	Remote Similarity	NPC27507
0.6543	Remote Similarity	NPC474418
0.6506	Remote Similarity	NPC469750
0.6429	Remote Similarity	NPC76572
0.6429	Remote Similarity	NPC193382
0.6333	Remote Similarity	NPC475629
0.6222	Remote Similarity	NPC475556
0.6222	Remote Similarity	NPC311706
0.6196	Remote Similarity	NPC469749
0.619	Remote Similarity	NPC219085
0.6044	Remote Similarity	NPC32793
0.6044	Remote Similarity	NPC116075
0.6	Remote Similarity	NPC196429
0.593	Remote Similarity	NPC5311
0.593	Remote Similarity	NPC34390
0.587	Remote Similarity	NPC240070
0.5761	Remote Similarity	NPC27363
0.5747	Remote Similarity	NPC77299
0.5747	Remote Similarity	NPC480906
0.5747	Remote Similarity	NPC480915
0.573	Remote Similarity	NPC179412
0.573	Remote Similarity	NPC471356
0.573	Remote Similarity	NPC471353
0.5682	Remote Similarity	NPC10823
0.5682	Remote Similarity	NPC480914
0.5625	Remote Similarity	NPC146857
0.5625	Remote Similarity	NPC247190
0.5568	Remote Similarity	NPC484210
0.5532	Remote Similarity	NPC471357
0.5532	Remote Similarity	NPC469757
0.5532	Remote Similarity	NPC117702
0.5484	Remote Similarity	NPC30483
0.5484	Remote Similarity	NPC470897
0.5444	Remote Similarity	NPC180079
0.5435	Remote Similarity	NPC480907
0.5426	Remote Similarity	NPC236973
0.5393	Remote Similarity	NPC6108
0.5393	Remote Similarity	NPC89514
0.5368	Remote Similarity	NPC608063
0.5341	Remote Similarity	NPC471633
0.5263	Remote Similarity	NPC32177
0.5263	Remote Similarity	NPC292467
0.5263	Remote Similarity	NPC469756
0.5263	Remote Similarity	NPC275901
0.5258	Remote Similarity	NPC486143
0.5258	Remote Similarity	NPC486142
0.5258	Remote Similarity	NPC486149
0.5243	Remote Similarity	NPC329675
0.5243	Remote Similarity	NPC194716
0.5217	Remote Similarity	NPC471359
0.5208	Remote Similarity	NPC188234
0.5208	Remote Similarity	NPC480910
0.5208	Remote Similarity	NPC480909
0.5165	Remote Similarity	NPC199428
0.5165	Remote Similarity	NPC243196
0.5165	Remote Similarity	NPC109448
0.5165	Remote Similarity	NPC310341
0.5109	Remote Similarity	NPC146456
0.5106	Remote Similarity	NPC72260
0.5102	Remote Similarity	NPC486135
0.5102	Remote Similarity	NPC486137
0.5062	Remote Similarity	NPC160583
0.5052	Remote Similarity	NPC486130
0.5051	Remote Similarity	NPC232785
0.5051	Remote Similarity	NPC486139

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC86182 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6059
0.1-0.2	2977
0.2-0.3	97
0.3-0.4	4
0.4-0.5	9
0.5-0.6	1
0.6-0.7	0
0.7-0.8	3
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
0.7595	Intermediate Similarity	NPD7327	Approved
0.7595	Intermediate Similarity	NPD7328	Phase 4
0.7564	Intermediate Similarity	NPD7319	Approved
0.5106	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