NPASS Compound

Natural Product: NPC195239

Natural Product ID	NPC195239
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Procheatoglobosin Ii
IUPAC Name	n.a.
Synonyms	Procheatoglobosin Ii
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL486056
PubChem CID	11752332
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001819] Isoindoles and derivatives [CHEMONTID:0002496] Isoindolines [CHEMONTID:0001820] Isoindolones

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 73 77 0 0 0 0 0 0 0 0999 V2000 5.5173 -1.0674 -2.3679 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6144 -0.4592 -1.2847 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5612 0.2989 -1.9807 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5293 1.0117 -1.2662 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2795 1.2108 -0.0041 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0778 2.0193 0.4584 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7836 3.0371 -0.5511 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3851 3.6401 -0.5882 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7026 4.6749 -1.6056 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 3.3081 0.4069 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7893 3.6975 -0.1634 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3738 1.9337 0.9219 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4341 1.0265 0.3109 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2867 0.3658 1.3399 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2981 -0.4895 0.6493 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6244 -0.1482 0.3989 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2173 -1.1546 -0.2588 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.3540 -2.1623 -0.4653 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4936 -3.3958 -1.0836 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4123 -4.2447 -1.1409 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2312 -3.8564 -0.5904 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0872 -2.6253 0.0281 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1457 -1.7449 0.1063 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6982 0.1762 -0.5494 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4166 0.2079 -0.3459 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1016 1.1272 0.7344 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0962 0.4288 2.0363 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5893 0.9266 3.0492 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8897 -0.6867 2.4119 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7023 -1.4062 1.7219 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4578 -2.5319 2.2592 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3205 -2.9285 3.3510 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4630 -3.1395 1.2724 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1261 -1.8864 0.6795 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0127 -1.6680 -0.5901 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8429 -1.0721 1.6907 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3847 -0.6139 -1.1733 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4405 -0.4534 -3.3106 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1746 -2.0789 -2.6581 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5768 -1.0236 -2.0681 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2622 0.1018 -0.6208 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0274 1.0549 -2.6992 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0605 -0.4223 -2.7133 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7884 1.5059 -1.9664 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9055 0.8660 0.8083 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3056 2.5482 1.4096 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5256 3.3410 -1.3012 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4135 4.2435 -2.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2119 5.0694 -2.0979 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2105 5.5656 -1.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2833 4.0129 1.2848 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9093 3.4369 -1.2231 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6247 3.3988 0.4896 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8133 4.8291 -0.1446 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6027 1.9549 2.0213 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1198 1.6279 -0.3469 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7405 -0.2937 2.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8439 1.1181 1.9227 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0376 0.8119 0.7231 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2080 -1.1488 -0.5634 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4361 -3.6703 -1.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4828 -5.2211 -1.6180 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3818 -4.5178 -0.6330 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1531 -2.3264 0.4702 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7619 -0.9679 3.5190 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8812 -1.2673 0.6968 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1494 -3.7642 1.8071 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9340 -3.6185 0.4499 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4727 -2.3316 -1.2897 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1451 -0.4866 2.3415 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6001 -0.3973 1.3048 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3806 -1.7391 2.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0701 -1.5682 -1.2872 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 2 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 8 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 13 24 1 0 24 25 2 0 26 25 1 6 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 25 37 1 0 35 2 1 0 26 6 1 0 26 12 1 0 23 15 1 0 23 18 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 1 3 42 1 0 3 43 1 0 4 44 1 0 5 45 1 0 6 46 1 1 7 47 1 0 9 48 1 0 9 49 1 0 9 50 1 0 10 51 1 1 11 52 1 0 11 53 1 0 11 54 1 0 12 55 1 1 13 56 1 6 14 57 1 0 14 58 1 0 16 59 1 0 17 60 1 0 19 61 1 0 20 62 1 0 21 63 1 0 22 64 1 0 29 65 1 0 30 66 1 0 33 67 1 0 33 68 1 0 35 69 1 0 36 70 1 0 36 71 1 0 36 72 1 0 37 73 1 0 M END

Standard InCHIKey	ZWMGAOFPDWVLLV-JRSXRJALSA-N
Standard InCHI	InChI=1S/C32H36N2O3/c1-19-8-7-9-24-16-21(3)22(4)30-28(17-23-18-33-27-11-6-5-10-26(23)27)34-31(37)32(24,30)29(36)13-12-25(35)15-20(2)14-19/h5-7,9-14,16,18-19,22,24,28,30,33H,8,15,17H2,1-4H3,(H,34,37)/b9-7+,13-12+,20-14+/t19-,22+,24-,28-,30-,32+/m0/s1
SMILES	C[C@H]1C/C=C/[C@H]2C=C(C)[C@@H](C)[C@H]3[C@H](Cc4c[nH]c5ccccc45)N=C([C@@]23C(=O)/C=C/C(=O)C/C(=C/1)/C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	496.27	Volume:	538.609 ? Van der Waals volume.
Dense:	0.921	LogP:	3.526 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.22 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.372 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	34.0
TPSA:	82.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.466	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.954	Fsp³:	0.406
MCE-18:	135.022 ? 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:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.986	Fluc inhibitor:	0.352 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.298 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.423 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.01	Promiscuous compounds:	0.708

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.126	MDCK Permeability:	-4.749
Pgp-inhibitor:	0.895	Pgp-substrate:	0.172
PAMPA:	0.144 ? 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%):	0.181	30% Bioavailability (F30%):	0.554
50% Bioavailability (F50%):	0.858

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017	MRP1:	0.893
Plasma Protein Binding (PPB):	97.378%	Volume Distribution (VD):	0.315
Fu:	2.431% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.853
CYP2C19-inhibitor:	0.024	CYP2C19-substrate:	0.264
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.016	CYP2D6-substrate:	0.834
CYP3A4-inhibitor:	0.965	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.882 ? 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):

9.028

Half-life (T1/2):

0.467

ADMET: Toxicity

hERG Blockers:	0.06	hERG Blockers (10um):	0.046
Human Hepatotoxicity (H-HT):	0.999	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.702	Rat Oral Acute Toxicity:	0.202
Maximum Recommended Daily Dose:	0.959	Skin Sensitization:	1.0
Carcinogencity:	0.734	Eye Corrosion:	0.0
Eye Irritation:	0.461	Respiratory Toxicity:	0.93
Drug-induced Neurotoxicity:	0.834	Ototoxicity:	0.783
Hematotoxicity:	0.571	Drug-induced Nephrotoxicity:	0.975
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.153
A549 Cytotoxicity:	0.498	Hek293 Cytotoxicity:	0.89
BCF:	1.399 ? 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:	4.148 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.515 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.1 ? 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
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26217	Limacia cuspidata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26217	Limacia cuspidata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	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	4
IZ	1

Activity Type	# Activity
Cell line	4
Organism	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
NPT168	Cell line	P388	Mus musculus	IC50	=	3.99	ug.mL-1	PMID[15497948]
NPT400	Cell line	MDA-MB-435	Homo sapiens	IC50	=	36880.0	nM	PMID[30015071]
NPT515	Cell line	SGC-7901	Homo sapiens	IC50	=	37700.0	nM	PMID[30015071]
NPT81	Cell line	A549	Homo sapiens	IC50	=	35930.0	nM	PMID[30015071]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	2.0	mm	PMID[15497948]

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 NPC195239 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	19335
0.1-0.2	29148
0.2-0.3	1133
0.3-0.4	195
0.4-0.5	15
0.5-0.6	17
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8795	High Similarity	NPC157828
0.8	Intermediate Similarity	NPC225821
0.7889	Intermediate Similarity	NPC98715
0.7717	Intermediate Similarity	NPC46225
0.7128	Intermediate Similarity	NPC487662
0.7083	Intermediate Similarity	NPC487663
0.6979	Remote Similarity	NPC487664
0.6875	Remote Similarity	NPC487661
0.6495	Remote Similarity	NPC11445
0.6495	Remote Similarity	NPC271862
0.6465	Remote Similarity	NPC203614
0.6275	Remote Similarity	NPC235885
0.6238	Remote Similarity	NPC204491
0.6139	Remote Similarity	NPC141428
0.6139	Remote Similarity	NPC87856
0.5962	Remote Similarity	NPC57690
0.5962	Remote Similarity	NPC2395
0.5922	Remote Similarity	NPC151976
0.5743	Remote Similarity	NPC267965
0.5714	Remote Similarity	NPC605716
0.5714	Remote Similarity	NPC609303
0.5673	Remote Similarity	NPC258062
0.566	Remote Similarity	NPC487660
0.5631	Remote Similarity	NPC266192
0.5577	Remote Similarity	NPC132211
0.5514	Remote Similarity	NPC487658
0.5472	Remote Similarity	NPC127677
0.5472	Remote Similarity	NPC487657
0.5421	Remote Similarity	NPC267926
0.5413	Remote Similarity	NPC487659
0.5248	Remote Similarity	NPC610239
0.5185	Remote Similarity	NPC147446

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC195239 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3636
0.1-0.2	5338
0.2-0.3	135
0.3-0.4	41
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