NPASS Compound

Natural Product: NPC18775

Natural Product ID	NPC18775
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OLFMGIZTWHFEJC-SJOOQERCSA-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: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 85 89 0 0 0 0 0 0 0 0999 V2000 4.4163 -2.6073 -0.1874 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2564 -1.6572 -0.5912 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8946 -0.7457 -1.6092 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9372 0.1658 -1.0790 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3533 0.9368 0.0867 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3857 1.9268 -0.4457 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8067 -0.0062 1.1142 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8146 -1.0042 0.6690 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3937 -0.6502 0.7401 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9457 0.0714 1.7464 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4564 0.5129 1.9690 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2840 0.1579 0.7893 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7614 0.4702 0.9551 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3855 -0.1303 2.1699 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8573 1.9826 1.1066 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8365 2.6376 0.2081 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1205 1.9269 -0.0229 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8365 0.5469 -0.5070 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0894 0.5487 -2.0265 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8973 -0.3762 0.0558 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1286 0.1137 -0.4389 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4406 0.0714 -0.3238 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3471 -1.3985 -0.5625 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8994 -1.7776 -0.7218 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9788 -1.1993 0.2921 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8492 -2.2297 1.4202 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4391 -1.1354 -0.3302 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3999 -0.2779 -1.5352 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9015 -2.5359 -0.6349 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2570 -2.5145 -1.2865 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9969 1.9674 1.0793 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4984 1.6669 0.6922 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7939 1.4413 1.8859 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2540 2.5895 -0.0129 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3287 3.2565 0.6009 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6201 -3.3170 -1.0122 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2907 -1.9885 0.0630 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1098 -3.1444 0.7384 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4224 -1.4464 -2.3262 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1615 -0.2251 -2.2095 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9091 -0.2832 -0.8674 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1259 0.9405 -1.8793 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8171 2.9440 -0.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4286 1.9794 0.1478 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1376 1.7876 -1.5184 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5737 0.5773 2.0137 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7293 -0.5964 1.4432 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9064 -1.8513 1.4502 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6662 0.3772 2.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7532 0.0277 2.9275 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4953 1.6167 2.0998 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9651 0.8962 -0.0141 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8840 -1.1071 2.0106 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7191 -0.2422 3.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2070 0.5371 2.5734 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0951 2.2700 2.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8692 2.4910 0.9050 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4129 2.9057 -0.7867 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0940 3.6347 0.6735 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6706 2.5391 -0.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9984 1.6087 -2.4072 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3300 -0.0166 -2.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0795 0.1776 -2.2872 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9491 -0.2719 1.1422 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8114 -1.4002 -0.3076 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6545 0.5420 0.2547 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8415 0.5654 -1.1467 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8616 -1.6840 -1.5063 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7796 -2.0341 0.2155 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8873 -2.9089 -0.6306 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6335 -1.5922 -1.7809 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9139 -3.2342 0.9049 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1245 -2.2224 1.9052 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7137 -2.2039 2.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0422 0.6272 -1.4746 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8137 -0.8375 -2.4261 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6015 0.1249 -1.8193 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2058 -3.0715 -1.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0453 -3.1203 0.3233 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5864 -3.6062 -1.3184 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2020 -2.2673 -2.3854 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5425 2.3945 1.8357 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6600 4.0522 -0.1059 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0635 3.7101 1.5664 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2104 2.6017 0.7566 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 6 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 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 18 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 25 27 1 0 27 28 1 6 27 29 1 0 29 30 1 0 17 31 1 0 5 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 30 2 1 0 8 2 1 0 27 9 1 0 25 12 1 0 22 13 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 6 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 8 48 1 1 10 49 1 0 11 50 1 0 11 51 1 0 12 52 1 6 14 53 1 0 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 6 19 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 21 66 1 0 22 67 1 6 23 68 1 0 23 69 1 0 24 70 1 0 24 71 1 0 26 72 1 0 26 73 1 0 26 74 1 0 28 75 1 0 28 76 1 0 28 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 30 81 1 0 31 82 1 0 35 83 1 0 35 84 1 0 35 85 1 0 M END

Standard InCHIKey	OLFMGIZTWHFEJC-SJOOQERCSA-N
Standard InCHI	InChI=1S/C31H50O4/c1-26-14-15-27(2,25(34)35-7)18-21(26)20-8-9-23-28(3)12-11-24(33)29(4,19-32)22(28)10-13-31(23,6)30(20,5)17-16-26/h8,21-24,32-33H,9-19H2,1-7H3/t21-,22+,23+,24-,26+,27-,28-,29+,30+,31+/m0/s1
SMILES	C[C@@]12CC[C@@](C)(C[C@H]2C2=CC[C@@H]3[C@@]4(C)CC[C@@H]([C@](C)(CO)[C@@H]4CC[C@@]3(C)[C@]2(C)CC1)O)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.37	Volume:	531.838 ? Van der Waals volume.
Dense:	0.915	LogP:	4.114 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.831 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.103 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	27.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.355	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.877	Fsp³:	0.903
MCE-18:	104.441 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.813	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? 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:	0.443	Promiscuous compounds:	0.101

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.254	MDCK Permeability:	-4.984
Pgp-inhibitor:	0.816	Pgp-substrate:	0.161
PAMPA:	0.974 ? 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):	0.0
20% Bioavailability (F20%):	0.987	30% Bioavailability (F30%):	0.22
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996	MRP1:	0.999
Plasma Protein Binding (PPB):	85.271%	Volume Distribution (VD):	-0.281
Fu:	9.64% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.42	BCRP inhibitor:	0.962
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.993	CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.886	CYP2C19-substrate:	0.385
CYP2C9-inhibitor:	0.122	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.089	CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.948	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.951
HLM stability:	0.774 ? 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):

9.486

Half-life (T1/2):

0.457

ADMET: Toxicity

hERG Blockers:	0.051	hERG Blockers (10um):	0.139
Human Hepatotoxicity (H-HT):	0.799	Drug-induced Liver Injury (DILI):	0.156
AMES Toxicity:	0.228	Rat Oral Acute Toxicity:	0.544
Maximum Recommended Daily Dose:	0.72	Skin Sensitization:	0.993
Carcinogencity:	0.99	Eye Corrosion:	0.026
Eye Irritation:	0.525	Respiratory Toxicity:	0.809
Drug-induced Neurotoxicity:	0.065	Ototoxicity:	0.44
Hematotoxicity:	0.473	Drug-induced Nephrotoxicity:	0.911
Genotoxicity:	0.891	RPMI-8226 Immunitoxicity:	0.058
A549 Cytotoxicity:	0.604	Hek293 Cytotoxicity:	0.608
BCF:	1.508 ? 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:	3.854 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.466 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.757 ? 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
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11164-015-2099-x]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1134/S1021443711030101]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	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 NPC18775 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	17437
0.1-0.2	26436
0.2-0.3	4719
0.3-0.4	985
0.4-0.5	204
0.5-0.6	56
0.6-0.7	14
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	Natural Product ID
0.75	Intermediate Similarity	NPC196753
0.6515	Remote Similarity	NPC246708
0.6462	Remote Similarity	NPC470588
0.6452	Remote Similarity	NPC290598
0.6452	Remote Similarity	NPC30590
0.6429	Remote Similarity	NPC263393
0.6338	Remote Similarity	NPC476879
0.6324	Remote Similarity	NPC213412
0.6324	Remote Similarity	NPC295643
0.6212	Remote Similarity	NPC230295
0.6212	Remote Similarity	NPC98386
0.6056	Remote Similarity	NPC49776
0.6056	Remote Similarity	NPC63118
0.6056	Remote Similarity	NPC474436
0.6029	Remote Similarity	NPC40552
0.5909	Remote Similarity	NPC101475
0.5821	Remote Similarity	NPC235341
0.5775	Remote Similarity	NPC488519
0.575	Remote Similarity	NPC237503
0.5735	Remote Similarity	NPC253402
0.5735	Remote Similarity	NPC53744
0.5692	Remote Similarity	NPC27765
0.5692	Remote Similarity	NPC122418
0.5692	Remote Similarity	NPC491014
0.5588	Remote Similarity	NPC478657
0.5584	Remote Similarity	NPC258547
0.5556	Remote Similarity	NPC171203
0.5556	Remote Similarity	NPC307426
0.5556	Remote Similarity	NPC98442
0.5556	Remote Similarity	NPC242468
0.5441	Remote Similarity	NPC311078
0.5362	Remote Similarity	NPC253807
0.5362	Remote Similarity	NPC40394
0.5362	Remote Similarity	NPC158662
0.5342	Remote Similarity	NPC270768
0.5342	Remote Similarity	NPC59263
0.5342	Remote Similarity	NPC210106
0.5342	Remote Similarity	NPC229281
0.5342	Remote Similarity	NPC121798
0.5342	Remote Similarity	NPC234346
0.5294	Remote Similarity	NPC476883
0.5286	Remote Similarity	NPC159168
0.5286	Remote Similarity	NPC95594
0.527	Remote Similarity	NPC61543
0.527	Remote Similarity	NPC293048
0.527	Remote Similarity	NPC225585
0.5263	Remote Similarity	NPC127689
0.5263	Remote Similarity	NPC294360
0.5211	Remote Similarity	NPC133954
0.5205	Remote Similarity	NPC136313
0.52	Remote Similarity	NPC164349
0.5169	Remote Similarity	NPC29069
0.5143	Remote Similarity	NPC195334
0.5143	Remote Similarity	NPC475862
0.5135	Remote Similarity	NPC7260
0.5135	Remote Similarity	NPC210037
0.5135	Remote Similarity	NPC120968
0.5135	Remote Similarity	NPC227467
0.5135	Remote Similarity	NPC273621
0.5132	Remote Similarity	NPC191412
0.5132	Remote Similarity	NPC114159
0.5132	Remote Similarity	NPC6818
0.5122	Remote Similarity	NPC167383
0.5119	Remote Similarity	NPC37739
0.5114	Remote Similarity	NPC476885
0.5109	Remote Similarity	NPC473373
0.5068	Remote Similarity	NPC477579
0.5065	Remote Similarity	NPC130520
0.5063	Remote Similarity	NPC283343
0.5059	Remote Similarity	NPC137917
0.5057	Remote Similarity	NPC476884

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC18775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6889
0.1-0.2	2183
0.2-0.3	74
0.3-0.4	1
0.4-0.5	2
0.5-0.6	0
0.6-0.7	1
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
0.6471	Remote Similarity	NPD7645	Phase 2

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