NPASS Compound

Natural Product: NPC472341

Natural Product ID	NPC472341
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NRHMKHNCVMMQCQ-YGBPDJJZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3359355
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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 91 95 0 0 0 0 0 0 0 0999 V2000 -8.4599 -0.8175 0.8941 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1480 -0.7580 1.0650 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3027 -0.0876 0.1891 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5876 1.3585 0.1951 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0203 1.7285 -0.2132 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7122 2.2223 -0.6845 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9229 -0.5033 0.6992 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7512 0.0297 -0.0219 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4649 -0.5621 0.6310 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2573 0.0044 -0.0635 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2632 1.5456 0.0421 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1759 1.9506 -0.1735 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9503 0.6640 -0.2442 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0536 -0.2824 0.5556 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0337 0.0581 2.0132 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6607 -1.6144 0.3999 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0427 -1.6535 0.9419 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9416 -0.5215 0.6803 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3095 0.7926 0.4450 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1588 1.8201 -0.1990 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1730 1.3579 -1.1593 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8533 0.0756 -0.8567 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2871 -0.7510 0.2155 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1514 -0.4083 1.6193 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7383 -2.1980 -0.0370 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2257 -2.2347 -0.2381 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8994 -0.9285 0.1251 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3687 0.2389 -0.6570 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0798 0.2078 -2.0184 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7220 1.5376 -0.0167 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8897 -0.7419 1.4888 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2252 0.1784 -1.6201 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5515 -2.0528 0.3524 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3965 -0.6969 -1.2086 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0284 -2.0346 -1.1140 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7294 -1.2818 -0.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8102 -1.6951 1.5903 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1193 -0.0207 1.2174 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5022 1.7316 1.2443 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6218 2.1049 0.6138 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4552 0.9233 -0.8207 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9839 2.6214 -0.9356 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3732 3.0028 -1.2148 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0730 2.8649 -0.0484 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1150 1.7029 -1.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9880 -1.6079 0.7982 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8938 -0.1681 1.7964 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7262 -0.1623 -1.0946 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6553 1.1235 0.2566 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5670 -0.3992 1.6812 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3606 -0.2090 -1.1356 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5760 1.9040 1.0163 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8976 1.9728 -0.7633 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2830 2.4557 -1.1623 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5529 2.6334 0.5933 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9909 -0.2206 2.5355 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7156 -0.6061 2.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1957 1.0952 2.2576 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0575 -2.3429 1.0058 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6562 -2.0144 -0.6352 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5166 -2.5866 0.5032 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9790 -1.9290 2.0391 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0499 1.2201 1.4629 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6709 2.4862 0.5601 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4631 2.5411 -0.7269 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7175 1.3862 -2.1955 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9848 2.1453 -1.2307 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7952 -0.5480 -1.8034 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4984 0.5621 1.9662 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2372 -1.1989 2.4051 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2591 -2.5978 -0.9639 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5150 -2.8371 0.8502 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5146 -2.4682 -1.2927 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7213 -3.0197 0.3848 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9824 -1.0610 -0.1677 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3949 0.4633 -2.8328 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9498 0.9162 -2.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4931 -0.8006 -2.2232 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0260 2.2984 -0.7939 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6749 1.3661 0.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0011 1.9324 0.6947 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7086 -0.3550 1.8525 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1258 -0.4681 -1.6511 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3400 1.0889 -2.2776 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4195 -0.4100 -2.0919 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3042 -2.6721 1.2158 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4860 -2.3444 -0.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7610 -2.2709 -0.4343 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3591 -0.5447 -1.6930 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6202 -0.2062 -1.8254 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7635 -2.4202 -1.9754 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 4 6 1 0 3 7 1 0 7 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 1 14 16 1 0 16 17 1 0 18 17 1 1 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 27 31 1 0 13 32 1 6 9 33 1 0 3 34 1 0 34 35 1 0 14 10 1 0 24 18 1 0 19 13 1 0 28 22 1 0 23 18 1 0 1 36 1 0 1 37 1 0 1 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 5 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 0 8 49 1 0 9 50 1 1 10 51 1 6 11 52 1 0 11 53 1 0 12 54 1 0 12 55 1 0 15 56 1 0 15 57 1 0 15 58 1 0 16 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 19 63 1 1 20 64 1 0 20 65 1 0 21 66 1 0 21 67 1 0 22 68 1 6 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 27 75 1 6 29 76 1 0 29 77 1 0 29 78 1 0 30 79 1 0 30 80 1 0 30 81 1 0 31 82 1 0 32 83 1 0 32 84 1 0 32 85 1 0 33 86 1 0 33 87 1 0 33 88 1 0 34 89 1 0 34 90 1 0 35 91 1 0 M END

Standard InCHIKey	NRHMKHNCVMMQCQ-YGBPDJJZSA-N
Standard InCHI	InChI=1S/C32H56O3/c1-21(2)32(20-33,35-8)16-11-22(3)23-12-14-29(7)25-10-9-24-27(4,5)26(34)13-15-30(24)19-31(25,30)18-17-28(23,29)6/h21-26,33-34H,9-20H2,1-8H3/t22-,23-,24+,25+,26+,28-,29+,30-,31+,32?/m1/s1
SMILES	COC(C(C)C)(CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O)C)C)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.42	Volume:	545.616 ? Van der Waals volume.
Dense:	0.895	LogP:	4.394 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.017 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.073 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	22.0
TPSA:	49.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.397	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.801	Fsp³:	1.0
MCE-18:	138.938 ? 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:	0.642	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.503	Promiscuous compounds:	0.122

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.396	MDCK Permeability:	-5.021
Pgp-inhibitor:	0.099	Pgp-substrate:	0.06
PAMPA:	0.09 ? 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):	0.001
20% Bioavailability (F20%):	0.09	30% Bioavailability (F30%):	0.459
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.406	MRP1:	0.025
Plasma Protein Binding (PPB):	92.206%	Volume Distribution (VD):	0.021
Fu:	9.653% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.965
BSEP inhibitor:	0.043

ADMET: Metabolism

CYP1A2-inhibitor:	0.017	CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.584
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.12
CYP2D6-inhibitor:	0.757	CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.288
HLM stability:	0.986 ? 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):

16.076

Half-life (T1/2):

0.844

ADMET: Toxicity

hERG Blockers:	0.092	hERG Blockers (10um):	0.298
Human Hepatotoxicity (H-HT):	0.482	Drug-induced Liver Injury (DILI):	0.013
AMES Toxicity:	0.323	Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.417	Skin Sensitization:	0.655
Carcinogencity:	0.879	Eye Corrosion:	0.001
Eye Irritation:	0.122	Respiratory Toxicity:	0.784
Drug-induced Neurotoxicity:	0.051	Ototoxicity:	0.725
Hematotoxicity:	0.342	Drug-induced Nephrotoxicity:	0.515
Genotoxicity:	0.025	RPMI-8226 Immunitoxicity:	0.068
A549 Cytotoxicity:	0.1	Hek293 Cytotoxicity:	0.295
BCF:	2.708 ? 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:	5.01 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.126 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.849 ? 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
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	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

Activity Type	# Activity
Ratio	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Ratio	=	9.4	n.a.	PMID[15921404]

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 NPC472341 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	24891
0.1-0.2	22502
0.2-0.3	2037
0.3-0.4	317
0.4-0.5	69
0.5-0.6	11
0.6-0.7	29
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
0.6981	Remote Similarity	NPC195530
0.6863	Remote Similarity	NPC41577
0.6731	Remote Similarity	NPC299948
0.6731	Remote Similarity	NPC241085
0.6731	Remote Similarity	NPC607543
0.6667	Remote Similarity	NPC470830
0.6667	Remote Similarity	NPC479659
0.6667	Remote Similarity	NPC273366
0.6604	Remote Similarity	NPC331618
0.6604	Remote Similarity	NPC257191
0.6604	Remote Similarity	NPC196358
0.6545	Remote Similarity	NPC473279
0.6545	Remote Similarity	NPC22133
0.6491	Remote Similarity	NPC473238
0.6491	Remote Similarity	NPC134481
0.6481	Remote Similarity	NPC200243
0.6481	Remote Similarity	NPC85346
0.6481	Remote Similarity	NPC254509
0.6481	Remote Similarity	NPC65897
0.6481	Remote Similarity	NPC82623
0.6481	Remote Similarity	NPC80237
0.6429	Remote Similarity	NPC76518
0.6364	Remote Similarity	NPC472342
0.6207	Remote Similarity	NPC89747
0.6182	Remote Similarity	NPC604180
0.6066	Remote Similarity	NPC195366
0.6066	Remote Similarity	NPC114743
0.6	Remote Similarity	NPC110923
0.6	Remote Similarity	NPC74296
0.5902	Remote Similarity	NPC483817
0.5738	Remote Similarity	NPC18384
0.569	Remote Similarity	NPC70982
0.5667	Remote Similarity	NPC606508
0.5593	Remote Similarity	NPC67872
0.5556	Remote Similarity	NPC85379
0.5556	Remote Similarity	NPC144909
0.5556	Remote Similarity	NPC476304
0.55	Remote Similarity	NPC12722
0.5484	Remote Similarity	NPC476186
0.5156	Remote Similarity	NPC307776

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472341 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7722
0.1-0.2	1390
0.2-0.3	36
0.3-0.4	2
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	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