NPASS Compound

Natural Product: NPC13743

Natural Product ID	NPC13743
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Roridin E Acetate
IUPAC Name	n.a.
Synonyms	Roridin E Acetate
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL452441
PubChem CID	44558998
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

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 80 84 0 0 0 0 0 0 0 0999 V2000 6.9374 0.5385 2.2856 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7995 0.7061 1.3516 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0011 1.7640 1.3063 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8868 1.8190 0.3202 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1002 0.5177 0.3740 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9977 -0.6665 0.5648 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4614 -0.3705 0.3507 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1851 0.6667 1.5602 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1516 -0.3022 1.5919 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1442 -0.2023 2.5488 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2593 0.7907 3.3450 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9864 -1.0855 2.7009 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2398 -2.1777 2.0365 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3869 -2.7595 0.9768 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5620 -2.8557 2.2919 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3288 -2.8137 0.9548 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5502 -1.4659 0.6139 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2329 -1.3145 -0.5416 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8540 -0.2313 -1.4271 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7273 0.4197 -1.6012 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7685 1.4663 -2.6075 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7934 2.2006 -2.9162 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4899 2.1840 -2.3938 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2534 3.1335 -2.9036 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1958 1.4270 -1.4949 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5723 1.6627 -1.1630 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3478 2.4212 -2.1984 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7764 1.8175 -2.0262 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3732 0.3716 -2.0185 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8734 -0.6979 -2.7326 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 -0.0032 -3.2953 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3327 0.3851 -0.9134 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4342 -0.8087 -1.0220 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3521 2.2065 -0.8811 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7516 -1.0313 -0.1663 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4676 -2.2313 0.2560 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7363 0.0828 0.6428 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1937 1.3260 0.3013 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6753 1.5263 -0.8203 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0784 2.4016 1.3425 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1394 -0.5411 2.3812 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7825 1.0506 3.2552 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8468 0.9653 1.7711 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2034 2.5757 2.0173 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2124 2.6410 0.7299 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9082 -1.0255 1.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7372 -1.5076 -0.0748 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6873 0.0487 -0.6285 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0217 -1.2890 0.5285 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 1.6486 1.6462 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8266 0.5849 2.4769 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7015 -0.7445 3.4999 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6720 -2.5314 1.1128 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5216 -3.9014 0.9679 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7090 -2.4717 -0.0321 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3614 -3.8912 2.5701 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1749 -2.3528 3.0356 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2935 -3.2722 1.1781 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8315 -3.3447 0.1557 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3671 -2.3180 -1.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7298 0.0988 -2.1123 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8012 0.2974 -1.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7067 1.5996 -3.1052 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9931 2.9677 -3.7144 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5363 2.2882 -0.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0776 2.0322 -3.2252 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3784 3.4932 -2.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4019 2.0718 -2.8815 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6352 -1.7385 -2.4602 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8960 -0.6307 -3.2037 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8524 -1.7561 -0.7025 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4014 -0.5737 -0.6647 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2686 -0.9431 -2.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2047 -0.6979 -1.1558 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4695 -2.4599 1.3433 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0969 -3.1268 -0.2865 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5534 -2.1639 -0.1052 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9254 2.3836 2.0500 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0903 2.3319 1.8202 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0907 3.3848 0.7965 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 1 6 7 1 0 5 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 32 33 1 1 28 34 1 0 18 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 7 2 1 0 32 26 1 0 34 4 1 0 32 5 1 0 29 31 1 6 1 41 1 0 1 42 1 0 1 43 1 0 3 44 1 0 4 45 1 1 6 46 1 0 6 47 1 0 7 48 1 0 7 49 1 0 8 50 1 0 8 51 1 0 12 52 1 0 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 18 60 1 6 19 61 1 0 20 62 1 0 21 63 1 0 22 64 1 0 26 65 1 1 27 66 1 0 27 67 1 0 28 68 1 6 30 69 1 0 30 70 1 0 33 71 1 0 33 72 1 0 33 73 1 0 35 74 1 6 36 75 1 0 36 76 1 0 36 77 1 0 40 78 1 0 40 79 1 0 40 80 1 0 M END

Standard InCHIKey	UMMRHXXIVGSHOW-JOAVBITDSA-N
Standard InCHI	InChI=1S/C31H40O9/c1-19-10-12-30-17-36-28(34)15-20(2)11-13-35-23(21(3)38-22(4)32)8-6-7-9-27(33)40-24-16-26(39-25(30)14-19)31(18-37-31)29(24,30)5/h6-9,14-15,21,23-26H,10-13,16-18H2,1-5H3/b8-6+,9-7-,20-15+/t21-,23-,24-,25-,26-,29-,30-,31+/m1/s1
SMILES	CC1=C[C@@H]2[C@@]3(CC1)COC(=O)/C=C(C)/CCO[C@H](/C=C/C=CC(=O)O[C@@H]1C[C@H]([C@@]4(CO4)[C@@]31C)O2)[C@@H](C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	556.27	Volume:	562.607 ? Van der Waals volume.
Dense:	0.989	LogP:	1.742 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.198 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.603 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	36.0
TPSA:	109.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.216	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.201	Fsp³:	0.645
MCE-18:	120.667 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.889	Fluc inhibitor:	0.028 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.021 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.137 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.314	Promiscuous compounds:	0.567

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.225	MDCK Permeability:	-4.701
Pgp-inhibitor:	0.147	Pgp-substrate:	0.73
PAMPA:	0.069 ? 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%):	0.67	30% Bioavailability (F30%):	0.672
50% Bioavailability (F50%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.995
Plasma Protein Binding (PPB):	95.54%	Volume Distribution (VD):	-0.081
Fu:	5.222% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.593
OATP1B3 inhibitor:	0.052	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.051	CYP3A4-substrate:	0.761
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.956
HLM stability:	0.612 ? 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):

6.836

Half-life (T1/2):

1.57

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.066
Human Hepatotoxicity (H-HT):	0.982	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.983	Rat Oral Acute Toxicity:	0.334
Maximum Recommended Daily Dose:	0.998	Skin Sensitization:	1.0
Carcinogencity:	0.442	Eye Corrosion:	0.0
Eye Irritation:	0.811	Respiratory Toxicity:	0.699
Drug-induced Neurotoxicity:	0.843	Ototoxicity:	0.476
Hematotoxicity:	0.415	Drug-induced Nephrotoxicity:	0.988
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.891
A549 Cytotoxicity:	0.74	Hek293 Cytotoxicity:	0.793
BCF:	0.732 ? 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:	3.485 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.385 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.728 ? 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
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075777]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[13678412]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21539317]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

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
EC50	4

Activity Type	# Activity
Cell line	2
Organism	1
Non-molecular	1

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
NPT91	Cell line	KB	Homo sapiens	EC50	=	0.014	ug.mL-1	PMID[22705001]
NPT189	Cell line	Vero	Chlorocebus aethiops	EC50	=	0.0041	ug.mL-1	Open TG-GATES in vivo data: Hematology
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	0.015	ug.mL-1	PMID[10075777]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	EC50	=	6e-05	ug.mL-1	PMID[22705001]

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 NPC13743 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	25857
0.1-0.2	23429
0.2-0.3	517
0.3-0.4	10
0.4-0.5	10
0.5-0.6	17
0.6-0.7	11
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8235	Intermediate Similarity	NPC98813
0.8235	Intermediate Similarity	NPC600365
0.7973	Intermediate Similarity	NPC29389
0.7973	Intermediate Similarity	NPC112316
0.7179	Intermediate Similarity	NPC108682
0.7162	Intermediate Similarity	NPC484152
0.7125	Intermediate Similarity	NPC484149
0.6706	Remote Similarity	NPC484153
0.6706	Remote Similarity	NPC484925
0.6386	Remote Similarity	NPC484923
0.6386	Remote Similarity	NPC484922
0.6375	Remote Similarity	NPC469959
0.6375	Remote Similarity	NPC469957
0.6341	Remote Similarity	NPC472263
0.6173	Remote Similarity	NPC98038
0.6173	Remote Similarity	NPC313921
0.6118	Remote Similarity	NPC101965
0.6118	Remote Similarity	NPC101400
0.5904	Remote Similarity	NPC469960
0.5904	Remote Similarity	NPC93026
0.5862	Remote Similarity	NPC474286
0.5862	Remote Similarity	NPC484150
0.5862	Remote Similarity	NPC484155
0.5824	Remote Similarity	NPC484154
0.575	Remote Similarity	NPC265502
0.5667	Remote Similarity	NPC475130
0.5667	Remote Similarity	NPC484145
0.5667	Remote Similarity	NPC484151
0.5647	Remote Similarity	NPC484920
0.5595	Remote Similarity	NPC65700
0.5529	Remote Similarity	NPC9579
0.5517	Remote Similarity	NPC484924
0.5275	Remote Similarity	NPC484144
0.5205	Remote Similarity	NPC234293
0.5169	Remote Similarity	NPC287075

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC13743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7723
0.1-0.2	1421
0.2-0.3	6
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	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