NPASS Compound

Natural Product: NPC29389

Natural Product ID	NPC29389
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Roridin E
IUPAC Name	n.a.
Synonyms	Roridin E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL509175
PubChem CID	44593339
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 75 79 0 0 0 0 0 0 0 0999 V2000 2.0684 4.0619 -0.2754 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3491 2.7181 -0.8389 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3972 1.7867 -0.8503 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0514 1.9886 -0.3320 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2006 3.0959 0.1279 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8774 1.0136 -0.3485 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1909 1.1612 0.1498 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0291 -0.0569 0.0674 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1939 0.1897 -0.8590 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9762 1.4363 -0.5306 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1703 1.5135 0.9213 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5780 0.7056 1.7701 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6384 -0.3920 1.4185 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3283 -1.5742 1.4206 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7283 -2.6534 0.8418 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3864 -2.3432 -0.5933 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3252 -1.2914 -0.4314 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5868 -1.1230 -1.7073 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4420 -1.9166 0.6328 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4479 -2.6250 -0.1094 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8873 -2.1216 -0.0908 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0265 -1.1497 0.5811 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8002 -2.8592 -0.8801 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0166 -2.5619 -1.0532 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7581 -1.4810 -0.5405 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7298 -0.4443 0.1954 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0293 0.4001 0.3503 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6464 1.6740 0.7225 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7501 2.6279 -0.2603 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7360 2.4562 -1.3850 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9643 -0.2126 1.3093 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1538 0.5384 1.4494 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3969 -1.6186 1.0311 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3084 -2.8695 1.3905 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9874 -2.8298 -1.7321 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8906 -3.5880 -1.2210 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1120 2.6003 1.3969 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2347 4.5830 -0.8065 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0052 4.6611 -0.3410 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8343 3.9366 0.7923 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5615 0.8092 -1.2532 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0682 1.4427 1.2368 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6146 2.0532 -0.3554 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8812 -0.7076 -0.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8117 0.3271 -1.8782 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9595 1.3221 -1.0742 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5275 2.3461 -0.9759 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8085 0.8684 2.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8422 -0.3731 2.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3377 -3.5430 0.9803 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 -0.8781 -1.6463 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6323 -2.1234 -2.2375 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0291 -0.4187 -2.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9795 -1.1481 1.2868 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4411 -3.7767 -1.3945 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5465 -3.3178 -1.7358 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8428 -1.5834 -1.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9104 -0.0657 0.7465 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4573 0.4395 -0.6696 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6267 3.6171 0.1641 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7888 2.5205 -0.6911 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9624 3.2188 -2.1431 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8269 1.4694 -1.8350 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5160 -0.1924 2.3355 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6552 0.2607 2.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1225 -1.9793 1.8147 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5632 -2.3665 1.0971 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9299 -1.7543 0.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0649 -3.9281 1.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3059 -2.6748 2.4810 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9973 -3.3231 -1.6738 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7817 -2.4403 -2.7306 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5450 3.5346 1.4103 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9660 2.6434 0.6793 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5063 2.2848 2.3753 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 2 0 4 6 1 0 6 7 1 0 8 7 1 1 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 27 31 1 0 31 32 1 0 31 33 1 0 19 34 1 0 16 35 1 0 35 36 1 0 11 37 1 0 30 2 1 0 13 8 1 0 34 15 1 0 17 8 1 0 16 36 1 6 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 7 42 1 0 7 43 1 0 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 12 48 1 0 13 49 1 1 15 50 1 6 18 51 1 0 18 52 1 0 18 53 1 0 19 54 1 1 23 55 1 0 24 56 1 0 25 57 1 0 26 58 1 0 27 59 1 6 29 60 1 0 29 61 1 0 30 62 1 0 30 63 1 0 31 64 1 1 32 65 1 0 33 66 1 0 33 67 1 0 33 68 1 0 34 69 1 0 34 70 1 0 35 71 1 0 35 72 1 0 37 73 1 0 37 74 1 0 37 75 1 0 M END

Standard InCHIKey	KEEQQEKLEZRLDS-FLGSVKSYSA-N
Standard InCHI	InChI=1S/C29H38O8/c1-18-9-11-28-16-34-26(32)14-19(2)10-12-33-21(20(3)30)7-5-6-8-25(31)37-22-15-24(36-23(28)13-18)29(17-35-29)27(22,28)4/h5-8,13-14,20-24,30H,9-12,15-17H2,1-4H3/b7-5+,8-6-,19-14+/t20-,21-,22-,23-,24-,27-,28-,29+/m1/s1
SMILES	C/C/1=CC(=O)OC[C@]23CCC(=C[C@H]2O[C@H]2[C@]4([C@]3(C)[C@H](OC(=O)/C=CC=C[C@@H](OCC1)[C@H](O)C)C2)CO4)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	514.26	Volume:	521.861 ? Van der Waals volume.
Dense:	0.985	LogP:	1.16 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.677 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.96 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	35.0
TPSA:	103.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.323	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.145	Fsp³:	0.655
MCE-18:	118.25 ? 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:	0.902	Fluc inhibitor:	0.046 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.043 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.067 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.149	Promiscuous compounds:	0.371

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.517	MDCK Permeability:	-5.027
Pgp-inhibitor:	0.046	Pgp-substrate:	0.228
PAMPA:	0.976 ? 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%):	0.008	30% Bioavailability (F30%):	0.054
50% Bioavailability (F50%):	0.859

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.52
Plasma Protein Binding (PPB):	96.67%	Volume Distribution (VD):	-0.154
Fu:	3.878% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.872	BCRP inhibitor:	0.354
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.03	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.858	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.152
HLM stability:	0.137 ? 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):

6.005

Half-life (T1/2):

2.286

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.055
Human Hepatotoxicity (H-HT):	0.972	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.946	Rat Oral Acute Toxicity:	0.379
Maximum Recommended Daily Dose:	0.996	Skin Sensitization:	1.0
Carcinogencity:	0.297	Eye Corrosion:	0.0
Eye Irritation:	0.647	Respiratory Toxicity:	0.868
Drug-induced Neurotoxicity:	0.517	Ototoxicity:	0.781
Hematotoxicity:	0.409	Drug-induced Nephrotoxicity:	0.985
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.891
A549 Cytotoxicity:	0.451	Hek293 Cytotoxicity:	0.773
BCF:	0.683 ? 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:	3.436 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.322 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.56 ? 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]
NPO29965	Myrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	Palau	n.a.	PMID[11277768]
NPO29965	Myrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027756]
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]
NPO7578	Trichoderma cornu-damae	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30457333]
NPO6563	Paramyrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117520]
NPO10303	Cercophora areolata	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792624]
NPO29965	Myrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6563	Paramyrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10303	Cercophora areolata	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7578	Trichoderma cornu-damae	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29965	Myrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6563	Paramyrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10303	Cercophora areolata	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6563	Paramyrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7578	Trichoderma cornu-damae	Species	Hypocreaceae	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
IC50	10
Activity	2
IZ	1
EC50	4

Activity Type	# Activity
Cell line	11
Organism	4
Non-molecular	2

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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	0.0003	ug.mL-1	PMID[21546135]
NPT137	Cell line	L1210	Mus musculus	IC50	=	0.0002	ug.mL-1	PMID[8691213]
NPT91	Cell line	KB	Homo sapiens	EC50	=	0.0005	ug.mL-1	PMID[18293903]
NPT189	Cell line	Vero	Chlorocebus aethiops	EC50	=	0.0004	ug.mL-1	PMID[9917310]
NPT81	Cell line	A549	Homo sapiens	IC50	<	9700.0	nM	PMID[25559759]
NPT457	Cell line	BT-549	Homo sapiens	IC50	=	0.02	nM	PMID[30457333]
NPT2459	Cell line	HCC70	Homo sapiens	IC50	=	0.02	nM	PMID[30457333]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	0.03	nM	PMID[30457333]
NPT784	Cell line	MDA-MB-468	Homo sapiens	IC50	=	0.05	nM	PMID[30457333]
NPT111	Cell line	K562	Homo sapiens	IC50	=	540.0	nM	PMID[31117520]
NPT2482	Cell line	SW 1116	Homo sapiens	IC50	=	39.0	nM	PMID[31117520]
NPT3095	Organism	Sordaria fimicola	Sordaria fimicola	Activity	=	100.0	%	PMID[23002419]
NPT3096	Organism	Ascobolus	Ascobolus	Activity	=	100.0	%	PMID[23002419]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	29.0	mm	PMID[12105963]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	7.6	10'-10 uM	PMID[12027756]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	0.0007	ug.mL-1	PMID[10075777]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	EC50	=	0.00015	ug.mL-1	PMID[18537291]

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
-	Mus musculus	LD50	=	55.0	mg/kg	ToxVal

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 NPC29389 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	19329
0.1-0.2	28997
0.2-0.3	1453
0.3-0.4	33
0.4-0.5	8
0.5-0.6	6
0.6-0.7	16
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC112316
0.9014	High Similarity	NPC108682
0.8904	High Similarity	NPC484149
0.8333	Intermediate Similarity	NPC484153
0.8333	Intermediate Similarity	NPC484925
0.8116	Intermediate Similarity	NPC98813
0.8116	Intermediate Similarity	NPC600365
0.7973	Intermediate Similarity	NPC13743
0.7692	Intermediate Similarity	NPC101965
0.7692	Intermediate Similarity	NPC101400
0.7534	Intermediate Similarity	NPC484152
0.75	Intermediate Similarity	NPC469960
0.75	Intermediate Similarity	NPC93026
0.7179	Intermediate Similarity	NPC484920
0.7143	Intermediate Similarity	NPC65700
0.7	Intermediate Similarity	NPC484924
0.6923	Remote Similarity	NPC469959
0.6923	Remote Similarity	NPC469957
0.6914	Remote Similarity	NPC484923
0.6914	Remote Similarity	NPC484922
0.6709	Remote Similarity	NPC98038
0.6709	Remote Similarity	NPC313921
0.6667	Remote Similarity	NPC472263
0.6353	Remote Similarity	NPC474286
0.6353	Remote Similarity	NPC484150
0.6353	Remote Similarity	NPC484155
0.6282	Remote Similarity	NPC265502
0.6136	Remote Similarity	NPC475130
0.6136	Remote Similarity	NPC484145
0.6136	Remote Similarity	NPC484151
0.6111	Remote Similarity	NPC484154
0.6024	Remote Similarity	NPC9579
0.5952	Remote Similarity	NPC305044
0.5952	Remote Similarity	NPC265290
0.573	Remote Similarity	NPC484144
0.5222	Remote Similarity	NPC484919
0.5135	Remote Similarity	NPC234293
0.5111	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 NPC29389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7050
0.1-0.2	2081
0.2-0.3	19
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