NPASS Compound

Natural Product: NPC242299

Natural Product ID	NPC242299
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SHCBCKBYTHZQGZ-XUIOTSDSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	51066493
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 86 89 0 0 0 0 0 0 0 0999 V2000 6.7605 -0.5826 -1.7198 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0085 -1.0043 -0.3180 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4417 -0.3366 0.6619 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5709 0.8169 0.3623 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1488 0.5982 0.8955 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3261 1.7923 0.5609 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9959 2.9957 1.2383 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8919 1.7315 0.8917 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5876 1.5280 2.3625 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1011 1.1242 2.2184 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2298 0.0525 1.2117 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9392 -1.1081 1.9191 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1101 0.6566 0.1565 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4659 1.2848 -0.9975 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8787 0.7613 -1.4468 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7266 0.5426 -0.2189 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1770 0.5029 -0.3523 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7487 1.7366 0.4091 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5933 0.8172 -1.7857 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0991 0.9792 -1.7798 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7351 -0.3482 -1.6162 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9080 -1.3097 -0.8404 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9273 -2.0875 0.0357 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3745 -2.3360 -1.7783 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9497 -0.6804 0.1198 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1516 -1.7102 0.8847 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9633 -1.0762 1.5905 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0260 -0.5066 0.6016 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5532 -1.6013 -0.3274 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8029 -2.8166 0.1175 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0313 -0.1821 -1.0836 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3198 2.6866 -0.8526 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4619 2.0267 -0.8143 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9007 -2.1798 -0.0952 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1552 0.4432 -1.8681 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2630 -1.2418 -2.4523 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6635 -0.6217 -1.9623 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6247 -0.6465 1.6798 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5721 1.0030 -0.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0359 1.7040 0.8456 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2638 0.4393 1.9873 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8047 -0.3221 0.3699 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2483 3.7910 1.4565 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7483 3.4595 0.5626 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4454 2.7104 2.2115 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4631 2.7571 0.6745 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1966 0.7480 2.8063 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 2.4766 2.9344 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3949 2.0490 1.9545 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2505 0.7784 3.2151 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0534 -0.9117 3.0257 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3989 -2.0499 1.8794 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9494 -1.2734 1.5440 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8707 -0.0706 -0.1949 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1400 1.1867 -1.8984 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2873 1.5865 -2.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7961 -0.0863 -2.1290 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4766 1.5019 0.3609 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6812 1.4868 0.9296 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7630 2.6314 -0.1969 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0170 1.9569 1.2453 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2204 0.1230 -2.5277 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2393 1.8792 -2.0027 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3785 1.4858 -2.7394 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3687 1.6737 -0.9534 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9354 -0.7342 -2.6622 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4763 -3.0644 0.3344 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8320 -2.3220 -0.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2165 -1.4953 0.9121 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3232 -2.2072 -2.0736 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0002 -2.3619 -2.7236 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4680 -3.3846 -1.3958 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6722 -0.3063 0.9287 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7487 -2.1635 1.7383 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4081 -0.2180 2.1749 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5763 -1.8117 2.2907 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2109 -1.7728 -1.1974 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4498 -1.4055 -0.7510 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4793 -2.5958 0.1564 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5931 -3.5699 0.7239 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6959 -0.7619 -1.5281 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0015 3.0296 -1.7301 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4982 1.1979 -1.3358 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4988 -2.8584 0.6842 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9144 -1.8709 0.2665 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0612 -2.7380 -1.0362 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 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 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 26 30 1 0 21 31 1 0 14 32 1 0 6 33 1 6 2 34 1 0 13 8 1 0 28 16 1 0 28 11 1 0 25 17 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 7 43 1 0 7 44 1 0 7 45 1 0 8 46 1 0 9 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 12 51 1 0 12 52 1 0 12 53 1 0 13 54 1 6 14 55 1 6 15 56 1 0 15 57 1 0 16 58 1 1 18 59 1 0 18 60 1 0 18 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 21 66 1 6 23 67 1 0 23 68 1 0 23 69 1 0 24 70 1 0 24 71 1 0 24 72 1 0 25 73 1 1 26 74 1 1 27 75 1 0 27 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 31 81 1 0 32 82 1 0 33 83 1 0 34 84 1 0 34 85 1 0 34 86 1 0 M END

Standard InCHIKey	SHCBCKBYTHZQGZ-XUIOTSDSSA-N
Standard InCHI	InChI=1S/C30H52O4/c1-18(2)10-9-13-30(8,34)19-11-15-28(6)24(19)20(31)16-22-27(5)14-12-23(33)26(3,4)25(27)21(32)17-29(22,28)7/h10,19-25,31-34H,9,11-17H2,1-8H3/t19?,20-,21+,22+,23+,24-,25-,27-,28-,29+,30-/m1/s1
SMILES	CC(=CCC[C@](C)(C1CC[C@]2(C)[C@H]1[C@@H](C[C@H]1[C@@]3(C)CC[C@@H](C(C)(C)[C@H]3[C@H](C[C@]21C)O)O)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	476.39	Volume:	525.735 ? Van der Waals volume.
Dense:	0.906	LogP:	4.258 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.881 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.144 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	21.0
TPSA:	80.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.406	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.052	Fsp³:	0.933
MCE-18:	90.517 ? 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:	0.592	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.333	Promiscuous compounds:	0.27

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.02	MDCK Permeability:	-4.946
Pgp-inhibitor:	0.181	Pgp-substrate:	0.876
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):	0.002
20% Bioavailability (F20%):	0.92	30% Bioavailability (F30%):	0.635
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.981
Plasma Protein Binding (PPB):	84.681%	Volume Distribution (VD):	-0.417
Fu:	11.862% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.976	BCRP inhibitor:	0.768
BSEP inhibitor:	0.979

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.511	CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.777	CYP3A4-substrate:	0.925
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.963
HLM stability:	0.01 ? 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):

14.094

Half-life (T1/2):

1.55

ADMET: Toxicity

hERG Blockers:	0.039	hERG Blockers (10um):	0.261
Human Hepatotoxicity (H-HT):	0.415	Drug-induced Liver Injury (DILI):	0.018
AMES Toxicity:	0.191	Rat Oral Acute Toxicity:	0.252
Maximum Recommended Daily Dose:	0.646	Skin Sensitization:	0.946
Carcinogencity:	0.507	Eye Corrosion:	0.016
Eye Irritation:	0.391	Respiratory Toxicity:	0.733
Drug-induced Neurotoxicity:	0.042	Ototoxicity:	0.824
Hematotoxicity:	0.171	Drug-induced Nephrotoxicity:	0.687
Genotoxicity:	0.016	RPMI-8226 Immunitoxicity:	0.077
A549 Cytotoxicity:	0.323	Hek293 Cytotoxicity:	0.161
BCF:	1.462 ? 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:	3.765 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.533 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.624 ? 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
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	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 NPC242299 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	26438
0.1-0.2	20654
0.2-0.3	2502
0.3-0.4	205
0.4-0.5	32
0.5-0.6	16
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC322313
1.0	High Similarity	NPC102253
1.0	High Similarity	NPC236237
0.7636	Intermediate Similarity	NPC80530
0.7636	Intermediate Similarity	NPC273410
0.6897	Remote Similarity	NPC244385
0.6667	Remote Similarity	NPC138621
0.6333	Remote Similarity	NPC207013
0.6333	Remote Similarity	NPC6978
0.6333	Remote Similarity	NPC167037
0.5738	Remote Similarity	NPC301707
0.5667	Remote Similarity	NPC66407
0.5645	Remote Similarity	NPC3403
0.56	Remote Similarity	NPC47566
0.56	Remote Similarity	NPC129372
0.5484	Remote Similarity	NPC285761
0.5484	Remote Similarity	NPC34930
0.5455	Remote Similarity	NPC474574
0.5309	Remote Similarity	NPC473199
0.5195	Remote Similarity	NPC160734
0.5152	Remote Similarity	NPC470071
0.5152	Remote Similarity	NPC157422
0.5152	Remote Similarity	NPC100586
0.5152	Remote Similarity	NPC109457
0.5122	Remote Similarity	NPC473020
0.5075	Remote Similarity	NPC187471

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC242299 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8119
0.1-0.2	1002
0.2-0.3	28
0.3-0.4	0
0.4-0.5	0
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	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7525	Registered

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