NPASS Compound

Natural Product: NPC141428

Natural Product ID	NPC141428
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Chaetoglobosin Q
IUPAC Name	n.a.
Synonyms	Chaetoglobosin Q
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL443917
PubChem CID	11261310
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 78 82 0 0 0 0 0 0 0 0999 V2000 -6.4923 -0.6718 -0.6715 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0662 -0.4378 -0.1070 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2896 -1.6307 -0.4382 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9452 -1.9734 -0.1082 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9681 -1.4583 0.5635 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6121 -1.9237 0.8228 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2260 -3.3116 0.5762 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9455 -3.5575 1.5346 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3859 -4.9772 1.5232 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0598 -2.6020 1.2065 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7415 -3.1598 -0.0079 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6711 -1.1509 1.1318 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7216 -0.4720 0.2256 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8488 0.9928 0.4642 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9036 1.5979 -0.4348 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4384 1.1276 -1.5854 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3405 2.0408 -2.0196 N 0 0 0 0 0 0 0 0 0 0 0 0 5.3976 3.0880 -1.1700 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1427 4.2407 -1.1732 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9778 5.1483 -0.1425 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0916 4.9166 0.8696 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3544 3.7415 0.8425 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4904 2.8122 -0.1662 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2442 -0.8781 -1.0516 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9480 -1.1407 -1.0201 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4610 -0.9217 0.3022 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2640 0.3461 0.4351 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3582 1.0947 1.3814 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0517 0.7920 -0.7572 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9246 1.7346 -0.6554 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8184 2.3791 -1.5602 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8476 2.2890 -2.7027 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8584 3.2379 -0.8364 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4391 2.0137 0.0251 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5810 0.8821 -0.5869 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8284 2.3803 1.3980 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3047 4.0789 0.0781 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3145 -1.5560 -2.1726 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4510 -3.2183 2.7971 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2497 -4.1895 0.9102 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1570 0.0891 -0.2139 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8236 -1.6410 -0.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5087 -0.7174 -1.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2865 -0.3655 1.0151 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4046 -1.7538 -1.5880 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9842 -2.5151 -0.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6176 -2.9937 -0.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2248 -0.4798 1.0443 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4839 -1.7631 1.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0563 -3.5568 -0.4629 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3272 -5.0533 2.0987 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6051 -5.5769 2.0765 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4530 -5.4373 0.5203 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8053 -2.6829 2.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0862 -3.3130 -0.8721 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0454 -4.2098 0.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6601 -2.6911 -0.3238 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6468 -0.7116 2.1316 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7399 -0.8876 0.4981 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2645 1.1307 1.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9592 1.6006 0.2569 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1938 0.1986 -2.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9337 1.9820 -2.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8495 4.4729 -1.9383 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5674 6.0623 -0.1387 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9767 5.6373 1.6658 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6695 3.6000 1.6629 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8156 0.2897 -1.6313 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0109 2.1806 0.3679 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6677 3.5483 -1.4307 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3038 0.8569 -1.6730 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5437 1.6067 2.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2539 3.2944 1.7364 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9117 2.5645 1.4262 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4553 5.0145 -0.2131 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5886 -1.2115 -3.1048 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1408 -3.1686 3.4837 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9201 -5.1034 0.6955 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 1 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 33 37 1 0 25 38 1 0 8 39 1 1 7 40 1 0 35 2 1 0 26 6 1 0 26 12 1 0 23 15 1 0 23 18 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 1 3 45 1 0 3 46 1 0 4 47 1 0 5 48 1 0 6 49 1 1 7 50 1 6 9 51 1 0 9 52 1 0 9 53 1 0 10 54 1 1 11 55 1 0 11 56 1 0 11 57 1 0 12 58 1 1 13 59 1 1 14 60 1 0 14 61 1 0 16 62 1 0 17 63 1 0 19 64 1 0 20 65 1 0 21 66 1 0 22 67 1 0 29 68 1 0 30 69 1 0 33 70 1 6 35 71 1 0 36 72 1 0 36 73 1 0 36 74 1 0 37 75 1 0 38 76 1 0 39 77 1 0 40 78 1 0 M END

Standard InCHIKey	GXXPQGPTEVHUTJ-VOXRAUTJSA-N
Standard InCHI	InChI=1S/C32H38N2O6/c1-17-8-7-10-22-29(38)31(4,40)19(3)27-24(15-20-16-33-23-11-6-5-9-21(20)23)34-30(39)32(22,27)26(36)13-12-25(35)28(37)18(2)14-17/h5-7,9-14,16-17,19,22,24,27-29,33,37-38,40H,8,15H2,1-4H3,(H,34,39)/b10-7+,13-12+,18-14+/t17-,19-,22-,24-,27-,28+,29-,31+,32+/m0/s1
SMILES	C[C@H]1C/C=C/[C@H]2[C@@H]([C@@](C)([C@@H](C)[C@H]3[C@H](Cc4c[nH]c5ccccc45)N=C([C@@]23C(=O)/C=C/C(=O)[C@@H](/C(=C/1)/C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	546.27	Volume:	567.616 ? Van der Waals volume.
Dense:	0.962	LogP:	2.725 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.763 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.742 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	34.0
TPSA:	143.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.364	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.309	Fsp³:	0.469
MCE-18:	154.894 ? 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:	0.672	Fluc inhibitor:	0.445 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.089 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.165 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.01	Promiscuous compounds:	0.594

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.681	MDCK Permeability:	-4.945
Pgp-inhibitor:	0.027	Pgp-substrate:	0.961
PAMPA:	0.996 ? 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):	0.002
20% Bioavailability (F20%):	0.687	30% Bioavailability (F30%):	0.98
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.681
Plasma Protein Binding (PPB):	85.911%	Volume Distribution (VD):	-0.15
Fu:	12.637% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.002
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.101
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.026
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.027
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.967 ? 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):

4.227

Half-life (T1/2):

1.116

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.681	Rat Oral Acute Toxicity:	0.648
Maximum Recommended Daily Dose:	0.237	Skin Sensitization:	1.0
Carcinogencity:	0.809	Eye Corrosion:	0.0
Eye Irritation:	0.88	Respiratory Toxicity:	0.955
Drug-induced Neurotoxicity:	0.054	Ototoxicity:	0.774
Hematotoxicity:	0.58	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.085
A549 Cytotoxicity:	0.186	Hek293 Cytotoxicity:	0.34
BCF:	1.034 ? 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:	3.818 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.378 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.839 ? 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	n.a.	mycelium	n.a.	PMID[21548578]
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.	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]
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	1

Activity Type	# Activity
Cell line	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	=	2.19	ug.mL-1	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 NPC141428 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	12089
0.1-0.2	36134
0.2-0.3	1404
0.3-0.4	187
0.4-0.5	16
0.5-0.6	12
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8261	Intermediate Similarity	NPC203614
0.7872	Intermediate Similarity	NPC87856
0.7766	Intermediate Similarity	NPC225821
0.7604	Intermediate Similarity	NPC487663
0.7449	Intermediate Similarity	NPC57690
0.69	Remote Similarity	NPC204491
0.6765	Remote Similarity	NPC235885
0.66	Remote Similarity	NPC98715
0.6569	Remote Similarity	NPC151976
0.6471	Remote Similarity	NPC46225
0.6442	Remote Similarity	NPC2395
0.6154	Remote Similarity	NPC258062
0.6139	Remote Similarity	NPC195239
0.61	Remote Similarity	NPC157828
0.6078	Remote Similarity	NPC267965
0.6	Remote Similarity	NPC487664
0.5905	Remote Similarity	NPC132211
0.581	Remote Similarity	NPC487662
0.5714	Remote Similarity	NPC271862
0.5607	Remote Similarity	NPC487661
0.5596	Remote Similarity	NPC267926
0.5514	Remote Similarity	NPC266192
0.5505	Remote Similarity	NPC487657
0.5405	Remote Similarity	NPC487658
0.5364	Remote Similarity	NPC147446
0.5268	Remote Similarity	NPC487660
0.5089	Remote Similarity	NPC127677
0.5043	Remote Similarity	NPC487659

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC141428 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3428
0.1-0.2	5521
0.2-0.3	167
0.3-0.4	34
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