NPASS Compound

Natural Product: NPC157828

Natural Product ID	NPC157828
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Procheatoglobosin I
IUPAC Name	n.a.
Synonyms	Procheatoglobosin I
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL485061
PubChem CID	11271635
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 74 78 0 0 0 0 0 0 0 0999 V2000 -6.2885 0.3025 -0.8135 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1771 -0.2006 0.0462 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5107 -1.3912 -0.5472 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2951 -1.8071 0.1865 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1038 -1.8542 -0.4486 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8862 -2.2591 0.2365 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3865 -3.4968 -0.3581 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8600 -3.7524 -0.5556 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2902 -5.0669 -1.1786 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9283 -2.8106 -0.2099 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5218 -1.6333 0.5753 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1186 -1.1522 0.4196 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3368 -0.4519 1.6618 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0179 -0.7375 2.8104 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2762 0.6503 1.5569 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7615 1.2939 2.5772 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7098 2.4071 2.5889 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2430 2.9104 1.3207 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0776 2.0090 0.4905 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3715 0.7613 0.7804 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5813 2.6522 -0.7943 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1912 -0.1739 -0.6572 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3860 0.2072 -0.8312 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2892 -0.4216 0.0559 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8043 0.4196 1.1744 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5660 1.6005 0.6843 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1184 2.9014 0.6512 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1092 3.6809 0.1396 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1664 2.9140 -0.1506 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8489 1.6164 0.1807 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7419 0.5681 0.0005 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9777 0.8668 -0.5287 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2991 2.1593 -0.8605 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3963 3.1967 -0.6748 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8421 0.3487 -1.4610 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6234 -2.4809 -1.5377 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9305 -0.6188 -1.0229 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0047 0.9522 -0.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0255 0.6699 -1.7993 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8157 -0.7181 0.9197 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2480 -2.2329 -0.6074 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2258 -1.0865 -1.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3955 -2.0671 1.2337 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1032 -1.5822 -1.4880 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1822 -2.5655 1.3018 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1756 -4.2341 -0.6412 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9386 -5.8781 -0.4738 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7971 -5.1599 -2.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3758 -5.1136 -1.2829 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7019 -3.3732 0.4068 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7504 -1.7909 1.6503 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5574 0.9339 0.5863 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3880 0.9283 3.5650 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1409 3.2732 3.0723 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5027 2.1799 3.3541 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3423 3.2625 0.7090 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7792 3.8722 1.5392 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9573 0.4123 1.7552 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1306 3.6677 -0.8929 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1610 2.0937 -1.6726 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6539 2.8006 -0.8039 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1730 -0.7381 -0.5446 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5401 -0.2020 1.7683 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0480 0.7261 1.9253 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 3.2914 0.9630 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0315 4.7125 0.0051 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4682 -0.4555 0.2704 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6599 0.0363 -0.6620 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2831 2.3425 -1.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7082 4.1898 -0.9548 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6882 1.1072 -2.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4668 -3.3433 -2.2601 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7271 -2.4430 -1.4335 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1722 -1.6255 -2.0582 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 11 12 1 0 12 13 1 1 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 12 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 22 35 1 0 10 36 1 0 20 2 1 0 30 26 1 0 12 6 1 0 34 29 1 0 24 11 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 1 3 41 1 0 3 42 1 0 4 43 1 0 5 44 1 0 6 45 1 1 7 46 1 0 9 47 1 0 9 48 1 0 9 49 1 0 10 50 1 1 11 51 1 1 15 52 1 0 16 53 1 0 17 54 1 0 17 55 1 0 18 56 1 0 18 57 1 0 20 58 1 0 21 59 1 0 21 60 1 0 21 61 1 0 24 62 1 6 25 63 1 0 25 64 1 0 27 65 1 0 28 66 1 0 31 67 1 0 32 68 1 0 33 69 1 0 34 70 1 0 35 71 1 0 36 72 1 0 36 73 1 0 36 74 1 0 M END

Standard InCHIKey	PAFRQNXHHHYHMF-XPBHXYGASA-N
Standard InCHI	InChI=1S/C32H38N2O2/c1-20-10-5-8-15-29(35)32-25(12-9-11-21(2)16-20)17-22(3)23(4)30(32)28(34-31(32)36)18-24-19-33-27-14-7-6-13-26(24)27/h6-9,12-17,19,21,23,25,28,30,33H,5,10-11,18H2,1-4H3,(H,34,36)/b12-9+,15-8+,20-16+/t21-,23+,25-,28-,30-,32+/m0/s1
SMILES	C[C@H]1C/C=C/[C@H]2C=C(C)[C@H]([C@@H]3[C@@]2(C(=O)/C=C/CC/C(=C/1)/C)C(=N[C@H]3Cc1c[nH]c2c1cccc2)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	482.29	Volume:	532.455 ? Van der Waals volume.
Dense:	0.906	LogP:	3.758 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.302 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.422 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	33.0
TPSA:	65.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.441	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.858	Fsp³:	0.438
MCE-18:	131.739 ? 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:	0.985	Fluc inhibitor:	0.354 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.396 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.277 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.009	Promiscuous compounds:	0.498

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.163	MDCK Permeability:	-4.781
Pgp-inhibitor:	0.988	Pgp-substrate:	0.248
PAMPA:	0.012 ? 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%):	0.308	30% Bioavailability (F30%):	0.719
50% Bioavailability (F50%):	0.822

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033	MRP1:	0.793
Plasma Protein Binding (PPB):	97.502%	Volume Distribution (VD):	0.407
Fu:	2.141% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.948	BCRP inhibitor:	0.002
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.015	CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.392	CYP2C19-substrate:	0.402
CYP2C9-inhibitor:	0.139	CYP2C9-substrate:	0.329
CYP2D6-inhibitor:	0.11	CYP2D6-substrate:	0.706
CYP3A4-inhibitor:	0.91	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.721 ? 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):

8.39

Half-life (T1/2):

0.434

ADMET: Toxicity

hERG Blockers:	0.067	hERG Blockers (10um):	0.042
Human Hepatotoxicity (H-HT):	0.999	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.479	Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.904	Skin Sensitization:	1.0
Carcinogencity:	0.359	Eye Corrosion:	0.0
Eye Irritation:	0.653	Respiratory Toxicity:	0.918
Drug-induced Neurotoxicity:	0.77	Ototoxicity:	0.647
Hematotoxicity:	0.312	Drug-induced Nephrotoxicity:	0.941
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.115
A549 Cytotoxicity:	0.389	Hek293 Cytotoxicity:	0.851
BCF:	2.023 ? 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:	4.452 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.844 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.402 ? 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	1
IZ	1

Activity Type	# Activity
Cell line	1
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]
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 NPC157828 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	20144
0.1-0.2	28316
0.2-0.3	1137
0.3-0.4	209
0.4-0.5	19
0.5-0.6	17
0.6-0.7	8
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	NPC195239
0.8276	Intermediate Similarity	NPC98715
0.7978	Intermediate Similarity	NPC225821
0.7889	Intermediate Similarity	NPC46225
0.7363	Intermediate Similarity	NPC11445
0.7283	Intermediate Similarity	NPC487662
0.7128	Intermediate Similarity	NPC487664
0.7053	Intermediate Similarity	NPC487663
0.6842	Remote Similarity	NPC487661
0.6632	Remote Similarity	NPC271862
0.6429	Remote Similarity	NPC203614
0.6364	Remote Similarity	NPC204491
0.6238	Remote Similarity	NPC235885
0.61	Remote Similarity	NPC141428
0.61	Remote Similarity	NPC87856
0.604	Remote Similarity	NPC151976
0.5922	Remote Similarity	NPC57690
0.5922	Remote Similarity	NPC2395
0.5859	Remote Similarity	NPC267965
0.5833	Remote Similarity	NPC610239
0.5743	Remote Similarity	NPC266192
0.5686	Remote Similarity	NPC132211
0.5631	Remote Similarity	NPC258062
0.5619	Remote Similarity	NPC487658
0.5619	Remote Similarity	NPC487660
0.5577	Remote Similarity	NPC127677
0.5577	Remote Similarity	NPC487657
0.5524	Remote Similarity	NPC267926
0.5514	Remote Similarity	NPC487659
0.5354	Remote Similarity	NPC605716
0.5354	Remote Similarity	NPC609303
0.5283	Remote Similarity	NPC147446
0.5049	Remote Similarity	NPC603978

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC157828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4032
0.1-0.2	4946
0.2-0.3	128
0.3-0.4	44
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