NPASS Compound

Natural Product: NPC109951

Natural Product ID	NPC109951
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FCPRBNDLDDAHLC-PWEBOEAPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10054631
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 100105 0 0 0 0 0 0 0 0999 V2000 -6.8188 2.5463 -1.3017 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9984 1.6229 -0.3466 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8234 2.4710 0.8805 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9361 0.5150 -0.0179 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1448 -0.5445 0.7117 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2284 -1.2132 -0.2719 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3800 -0.2486 -1.0412 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7728 1.1737 -1.0107 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9487 -0.5597 -0.7649 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 -0.6568 -1.8252 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7100 -0.9613 -1.7955 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2821 -0.3601 -0.4655 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1886 -0.1004 -0.4415 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0118 -1.1403 -1.0973 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4342 1.1869 -1.2402 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8417 1.6539 -1.2191 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6613 1.2125 -0.0026 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8139 1.0151 1.1887 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6271 0.4176 2.3133 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5367 2.4563 1.7211 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7240 3.0785 2.0441 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5275 0.3010 0.9576 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2550 -0.8956 1.8038 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2833 -0.9354 1.9363 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9337 -1.1575 0.5835 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8448 -2.6543 0.4083 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3968 -0.7602 0.6040 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4663 0.5027 1.4677 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2989 -1.7368 1.2775 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4196 -2.2613 0.4258 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2921 -2.9392 1.3131 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4734 0.1602 -0.2903 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7906 0.3910 -0.4243 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6674 -0.5537 0.2969 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9663 0.2392 0.5888 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3419 0.8200 -0.7598 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5635 0.2461 -1.8982 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1990 0.3110 -1.7952 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6906 0.4461 -0.9680 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9354 -0.5495 1.1437 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2088 -1.1265 1.4454 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1625 -2.0068 -1.1650 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1834 -1.7529 -2.3973 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9761 -2.9841 -0.6663 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7079 2.2006 -2.3365 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8644 2.5550 -0.9956 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4169 3.5843 -1.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6250 3.2019 0.9811 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6738 1.8442 1.7798 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8709 3.0703 0.7823 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4554 0.0950 -0.9051 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6731 0.9210 0.7232 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6746 -0.1534 1.6035 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9183 -1.2869 1.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6060 -0.5563 -2.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8520 1.7859 -0.7074 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8582 1.6123 -2.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5920 -0.5082 -2.8058 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6631 -2.0704 -1.8055 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1673 -0.5846 -2.6520 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7491 0.6748 -0.4162 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3065 -1.8263 -1.6632 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5817 -1.8038 -0.4511 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6070 -0.7730 -1.9937 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7497 1.9394 -0.7796 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0999 1.0577 -2.2924 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8112 2.7637 -1.2648 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4348 1.3511 -2.1313 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3683 2.0861 0.1465 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2328 0.7715 3.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6637 -0.6771 2.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6177 0.9156 2.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1098 3.0063 0.8596 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8034 2.4465 2.5228 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7747 3.2345 3.0402 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7212 1.0624 1.2094 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6441 -1.8415 1.4347 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6096 -0.7832 2.8645 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4569 -1.7634 2.6362 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4827 0.0680 2.3651 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6487 -3.0676 -0.2222 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1076 -3.0157 -0.0074 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9038 -3.1673 1.3930 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4543 0.1208 2.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7174 1.2427 1.2556 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5193 0.8717 1.4322 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8048 -2.6182 1.7183 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8379 -1.2922 2.1744 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0842 -3.0188 -0.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4350 -3.8719 1.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0138 1.4467 -0.1250 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0203 -1.3847 -0.4171 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6473 1.0754 1.2433 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3530 1.9289 -0.7455 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9594 -0.7661 -2.1186 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8454 0.8596 -2.8041 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7377 -0.5564 -0.8499 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7062 -1.5027 0.9799 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7441 -1.9873 1.3326 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5456 -3.5848 -1.2792 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 18 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 25 27 1 0 27 28 1 1 27 29 1 0 29 30 1 0 30 31 1 0 17 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 34 41 1 0 6 42 1 6 42 43 2 0 42 44 1 0 8 2 1 0 27 9 1 0 38 33 1 0 30 6 1 0 25 12 1 0 22 13 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 7 55 1 6 8 56 1 0 8 57 1 0 10 58 1 0 11 59 1 0 11 60 1 0 12 61 1 6 14 62 1 0 14 63 1 0 14 64 1 0 15 65 1 0 15 66 1 0 16 67 1 0 16 68 1 0 17 69 1 1 19 70 1 0 19 71 1 0 19 72 1 0 20 73 1 0 20 74 1 0 21 75 1 0 22 76 1 0 23 77 1 0 23 78 1 0 24 79 1 0 24 80 1 0 26 81 1 0 26 82 1 0 26 83 1 0 28 84 1 0 28 85 1 0 28 86 1 0 29 87 1 0 29 88 1 0 30 89 1 6 31 90 1 0 33 91 1 1 34 92 1 6 35 93 1 1 36 94 1 1 37 95 1 0 37 96 1 0 39 97 1 0 40 98 1 0 41 99 1 0 44100 1 0 M END

Standard InCHIKey	FCPRBNDLDDAHLC-PWEBOEAPSA-N
Standard InCHI	InChI=1S/C35H56O9/c1-30(2)13-14-35(29(41)42)20(15-30)19-7-8-23-31(3)11-10-25(44-28-27(40)26(39)21(37)17-43-28)32(4,18-36)22(31)9-12-33(23,5)34(19,6)16-24(35)38/h7,20-28,36-40H,8-18H2,1-6H3,(H,41,42)/t20-,21-,22?,23+,24+,25-,26-,27+,28-,31-,32-,33+,34+,35+/m0/s1
SMILES	CC1(C)CC[C@]2([C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC[C@@H]([C@@](C)(CO)C4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	620.39	Volume:	636.416 ? Van der Waals volume.
Dense:	0.975	LogP:	2.904 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.224 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.959 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	156.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.204	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.428	Fsp³:	0.914
MCE-18:	129.075 ? 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:	0.836	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.165	Promiscuous compounds:	0.075

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.904	MDCK Permeability:	-5.192
Pgp-inhibitor:	0.0	Pgp-substrate:	0.01
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):	0.002
20% Bioavailability (F20%):	0.334	30% Bioavailability (F30%):	0.037
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.445	MRP1:	0.654
Plasma Protein Binding (PPB):	78.083%	Volume Distribution (VD):	-0.471
Fu:	15.0% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.476	BCRP inhibitor:	0.088
BSEP inhibitor:	0.378

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.416
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.087
HLM stability:	0.0 ? 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):

0.681

Half-life (T1/2):

1.626

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.015
Human Hepatotoxicity (H-HT):	0.796	Drug-induced Liver Injury (DILI):	0.621
AMES Toxicity:	0.606	Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.075	Skin Sensitization:	0.999
Carcinogencity:	0.818	Eye Corrosion:	0.0
Eye Irritation:	0.137	Respiratory Toxicity:	0.616
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	0.904
Hematotoxicity:	0.703	Drug-induced Nephrotoxicity:	0.965
Genotoxicity:	0.349	RPMI-8226 Immunitoxicity:	0.053
A549 Cytotoxicity:	0.723	Hek293 Cytotoxicity:	0.318
BCF:	1.248 ? 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:	3.894 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.562 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.676 ? 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
NPO12214	Leontice robustum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12214	Leontice robustum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12214	Leontice robustum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12214	Leontice robustum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12214	Leontice robustum	Species	Berberidaceae	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 NPC109951 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	19266
0.1-0.2	25153
0.2-0.3	4078
0.3-0.4	919
0.4-0.5	326
0.5-0.6	69
0.6-0.7	31
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8861	High Similarity	NPC242611
0.825	Intermediate Similarity	NPC28198
0.825	Intermediate Similarity	NPC476123
0.7667	Intermediate Similarity	NPC488516
0.7412	Intermediate Similarity	NPC31839
0.7381	Intermediate Similarity	NPC283849
0.7292	Intermediate Similarity	NPC488515
0.7174	Intermediate Similarity	NPC480424
0.7126	Intermediate Similarity	NPC100383
0.7021	Intermediate Similarity	NPC80843
0.6897	Remote Similarity	NPC177246
0.6863	Remote Similarity	NPC288205
0.6863	Remote Similarity	NPC51465
0.686	Remote Similarity	NPC204407
0.68	Remote Similarity	NPC75318
0.6596	Remote Similarity	NPC136877
0.6562	Remote Similarity	NPC488561
0.6548	Remote Similarity	NPC601365
0.6526	Remote Similarity	NPC59804
0.642	Remote Similarity	NPC228784
0.642	Remote Similarity	NPC324341
0.642	Remote Similarity	NPC601810
0.6413	Remote Similarity	NPC284807
0.6392	Remote Similarity	NPC6377
0.6392	Remote Similarity	NPC208381
0.6383	Remote Similarity	NPC127853
0.6354	Remote Similarity	NPC174679
0.6354	Remote Similarity	NPC279554
0.6346	Remote Similarity	NPC475486
0.6222	Remote Similarity	NPC606107
0.6211	Remote Similarity	NPC270667
0.6145	Remote Similarity	NPC201657
0.6139	Remote Similarity	NPC104400
0.6139	Remote Similarity	NPC10320
0.6117	Remote Similarity	NPC79718
0.61	Remote Similarity	NPC469945
0.6058	Remote Similarity	NPC37134
0.6055	Remote Similarity	NPC323341
0.6042	Remote Similarity	NPC76999
0.6	Remote Similarity	NPC222047
0.6	Remote Similarity	NPC291903
0.596	Remote Similarity	NPC127056
0.5943	Remote Similarity	NPC488209
0.5926	Remote Similarity	NPC475119
0.5918	Remote Similarity	NPC12288
0.5905	Remote Similarity	NPC276093
0.5872	Remote Similarity	NPC473824
0.5865	Remote Similarity	NPC481082
0.5865	Remote Similarity	NPC164419
0.5769	Remote Similarity	NPC139044
0.5755	Remote Similarity	NPC145899
0.5745	Remote Similarity	NPC286347
0.5729	Remote Similarity	NPC473538
0.5714	Remote Similarity	NPC73829
0.57	Remote Similarity	NPC56713
0.5699	Remote Similarity	NPC57362
0.5698	Remote Similarity	NPC471588
0.5641	Remote Similarity	NPC471385
0.5619	Remote Similarity	NPC471383
0.5586	Remote Similarity	NPC200788
0.5575	Remote Similarity	NPC166422
0.5568	Remote Similarity	NPC6255
0.5567	Remote Similarity	NPC294112
0.5556	Remote Similarity	NPC164194
0.5545	Remote Similarity	NPC280941
0.5545	Remote Similarity	NPC235772
0.5487	Remote Similarity	NPC133818
0.5487	Remote Similarity	NPC243680
0.5464	Remote Similarity	NPC256798
0.5437	Remote Similarity	NPC295371
0.5437	Remote Similarity	NPC472949
0.5413	Remote Similarity	NPC324875
0.5413	Remote Similarity	NPC292677
0.5413	Remote Similarity	NPC477191
0.5392	Remote Similarity	NPC25605
0.5385	Remote Similarity	NPC22956
0.5377	Remote Similarity	NPC180550
0.5377	Remote Similarity	NPC35405
0.537	Remote Similarity	NPC119794
0.534	Remote Similarity	NPC109079
0.53	Remote Similarity	NPC189884
0.53	Remote Similarity	NPC138334
0.53	Remote Similarity	NPC480938
0.5278	Remote Similarity	NPC257468
0.5258	Remote Similarity	NPC224121
0.5253	Remote Similarity	NPC475633
0.5248	Remote Similarity	NPC1046
0.5234	Remote Similarity	NPC473383
0.5192	Remote Similarity	NPC114441
0.5172	Remote Similarity	NPC219180
0.5172	Remote Similarity	NPC110308
0.5149	Remote Similarity	NPC475472
0.514	Remote Similarity	NPC114304
0.5135	Remote Similarity	NPC323359
0.5133	Remote Similarity	NPC11242
0.5133	Remote Similarity	NPC62725
0.5116	Remote Similarity	NPC480946
0.5116	Remote Similarity	NPC130577
0.5116	Remote Similarity	NPC142415
0.5116	Remote Similarity	NPC102683
0.5114	Remote Similarity	NPC120840
0.5091	Remote Similarity	NPC484832
0.5089	Remote Similarity	NPC488564
0.5089	Remote Similarity	NPC477192
0.5057	Remote Similarity	NPC270768
0.5057	Remote Similarity	NPC59263
0.5057	Remote Similarity	NPC210106
0.505	Remote Similarity	NPC191410
0.505	Remote Similarity	NPC195132
0.5043	Remote Similarity	NPC251263

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC109951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6093
0.1-0.2	2981
0.2-0.3	68
0.3-0.4	7
0.4-0.5	1
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	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

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