NPASS Compound

Natural Product: NPC267926

Natural Product ID	NPC267926
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Chaetoglobosin F
IUPAC Name	n.a.
Synonyms	Chaetoglobosin F; Cheatoglobosin F
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL443188
PubChem CID	23259927
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001821] Cytochalasans [CHEMONTID:0003767] Chaetoglobosins

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 77 82 0 0 0 0 0 0 0 0999 V2000 -5.4566 2.4620 -2.1871 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6760 1.3001 -1.7129 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2376 1.5242 -2.3672 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4763 0.3189 -1.8516 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3815 0.3855 -1.0975 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7066 -0.8537 -0.6283 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0301 -1.6149 -1.7285 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7158 -2.7353 -1.4229 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7311 -3.3392 -2.3157 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9297 -2.9199 0.0658 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9567 -3.9397 0.4020 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2565 -1.5995 0.7084 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3265 -0.8327 0.0073 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7006 -1.1599 0.5306 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7928 -0.4250 -0.1253 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5642 -0.9082 -1.1548 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4202 0.0657 -1.4987 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2317 1.1501 -0.7352 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8628 2.3819 -0.7054 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4315 3.3027 0.2282 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4222 3.0372 1.1037 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8014 1.8117 1.0667 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1993 0.8517 0.1438 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0138 0.5590 0.2630 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7872 0.6853 0.5967 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0736 -0.6394 0.6117 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6726 -0.7032 1.8774 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2662 0.1078 2.7561 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7933 -1.5275 2.3056 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1702 -0.8925 1.9519 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1894 0.5153 2.3891 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2959 1.3951 2.1147 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8734 1.9595 3.0841 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8523 1.7402 0.7826 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3848 1.1931 -0.2858 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9730 2.7369 0.8006 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8959 0.5882 3.7929 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1619 1.9068 0.9192 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6158 -2.9910 -1.9249 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5612 2.2742 -2.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2505 3.3754 -1.6048 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1590 2.7066 -3.2630 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0729 0.3505 -2.0843 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3650 1.4017 -3.4377 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8335 2.4669 -2.0819 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8411 -0.6720 -2.1091 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0257 1.3776 -0.8668 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5893 -1.5134 -0.2992 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0555 -1.1288 -2.7145 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4668 -3.1410 -3.3978 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6086 -4.4612 -2.2273 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7683 -3.0510 -2.1795 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0399 -3.2768 0.5105 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7015 -4.0210 -0.4061 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3827 -3.7447 1.4089 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5258 -4.9742 0.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5132 -1.7563 1.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3081 -1.0064 -1.1105 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9531 -2.2340 0.4996 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7047 -0.8904 1.6338 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4720 -1.9124 -1.5936 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1451 0.0037 -2.2597 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6601 2.5833 -1.4006 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9166 4.2843 0.2694 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1198 3.8081 1.8263 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0108 1.6072 1.7734 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7665 -1.6989 3.4011 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8550 -2.5396 1.8560 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5631 -1.2304 1.0296 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8425 -1.4373 2.7353 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2595 0.9911 1.9417 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5270 0.4875 -0.0983 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5435 2.6080 1.7732 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6489 3.7696 0.7004 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7396 2.5240 0.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7730 0.3958 4.2433 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6229 2.7771 0.7969 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 6 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 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 34 36 1 0 31 37 1 0 25 38 1 0 8 39 1 0 35 2 1 0 26 6 1 0 39 7 1 0 26 12 1 0 23 15 1 0 23 18 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 6 3 44 1 0 3 45 1 0 4 46 1 0 5 47 1 0 6 48 1 1 7 49 1 6 9 50 1 0 9 51 1 0 9 52 1 0 10 53 1 1 11 54 1 0 11 55 1 0 11 56 1 0 12 57 1 1 13 58 1 6 14 59 1 0 14 60 1 0 16 61 1 0 17 62 1 0 19 63 1 0 20 64 1 0 21 65 1 0 22 66 1 0 29 67 1 0 29 68 1 0 30 69 1 0 30 70 1 0 31 71 1 6 35 72 1 0 36 73 1 0 36 74 1 0 36 75 1 0 37 76 1 0 38 77 1 0 M END

Standard InCHIKey	KTFGDHPTDQFFRL-USMZZGTESA-N
Standard InCHI	InChI=1S/C32H38N2O5/c1-17-8-7-10-22-29-31(4,39-29)19(3)27-24(15-20-16-33-23-11-6-5-9-21(20)23)34-30(38)32(22,27)26(36)13-12-25(35)28(37)18(2)14-17/h5-7,9-11,14,16-17,19,22,24-25,27,29,33,35H,8,12-13,15H2,1-4H3,(H,34,38)/b10-7+,18-14+/t17-,19-,22-,24-,25-,27-,29-,31+,32+/m0/s1
SMILES	C[C@H]1C/C=C/[C@H]2[C@H]3[C@@](C)([C@@H](C)[C@H]4[C@H](Cc5c[nH]c6ccccc56)N=C([C@@]24C(=O)CC[C@@H](C(=O)/C(=C/1)/C)O)O)O3

Calculated Properties

Physi-Chem Properties

Molecular Weight:	530.28	Volume:	552.906 ? Van der Waals volume.
Dense:	0.959	LogP:	2.776 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.553 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.554 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	36.0
TPSA:	115.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.378	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.18	Fsp³:	0.531
MCE-18:	170.612 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.808	Fluc inhibitor:	0.119 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.18 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.095 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.005	Promiscuous compounds:	0.75

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.423	MDCK Permeability:	-4.886
Pgp-inhibitor:	0.919	Pgp-substrate:	0.992
PAMPA:	0.79 ? 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%):	0.561	30% Bioavailability (F30%):	0.886
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.862
Plasma Protein Binding (PPB):	93.885%	Volume Distribution (VD):	0.039
Fu:	6.312% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.959	BCRP inhibitor:	0.015
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.804
CYP3A4-inhibitor:	0.513	CYP3A4-substrate:	0.18
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.986 ? 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):

3.664

Half-life (T1/2):

1.081

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.009
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.956	Rat Oral Acute Toxicity:	0.792
Maximum Recommended Daily Dose:	0.071	Skin Sensitization:	1.0
Carcinogencity:	0.965	Eye Corrosion:	0.0
Eye Irritation:	0.205	Respiratory Toxicity:	0.484
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.955
Hematotoxicity:	0.762	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.054
A549 Cytotoxicity:	0.027	Hek293 Cytotoxicity:	0.231
BCF:	1.076 ? 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:	3.842 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.351 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.81 ? 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]
NPO32736	chaetomium globosum ifb-e019	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	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	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]
NPO26889	Chaetomium subaffine	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[436014]
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]
NPO26889	Chaetomium subaffine	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]
NPO26889	Chaetomium subaffine	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26889	Chaetomium subaffine	Species	Chaetomiaceae	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	2

Activity Type	# Activity
Cell line	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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	3.2	ug.mL-1	PMID[15497948]
NPT91	Cell line	KB	Homo sapiens	IC50	=	52000.0	nM	PMID[16499339]

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 NPC267926 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	11745
0.1-0.2	36678
0.2-0.3	1237
0.3-0.4	158
0.4-0.5	11
0.5-0.6	17
0.6-0.7	4
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8462	Intermediate Similarity	NPC266192
0.8191	Intermediate Similarity	NPC487657
0.8021	Intermediate Similarity	NPC487658
0.7653	Intermediate Similarity	NPC487660
0.75	Intermediate Similarity	NPC487662
0.7475	Intermediate Similarity	NPC57690
0.7245	Intermediate Similarity	NPC132211
0.7157	Intermediate Similarity	NPC487659
0.6961	Remote Similarity	NPC290529
0.6346	Remote Similarity	NPC487664
0.6275	Remote Similarity	NPC267965
0.6214	Remote Similarity	NPC271862
0.5943	Remote Similarity	NPC487661
0.5849	Remote Similarity	NPC98715
0.5648	Remote Similarity	NPC225821
0.5596	Remote Similarity	NPC141428
0.5596	Remote Similarity	NPC46225
0.5596	Remote Similarity	NPC203614
0.5596	Remote Similarity	NPC87856
0.5545	Remote Similarity	NPC204491
0.5545	Remote Similarity	NPC151976
0.5545	Remote Similarity	NPC487663
0.5524	Remote Similarity	NPC157828
0.5446	Remote Similarity	NPC235885
0.5446	Remote Similarity	NPC2395
0.5421	Remote Similarity	NPC195239
0.5315	Remote Similarity	NPC487665
0.531	Remote Similarity	NPC70155
0.5133	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 NPC267926 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3373
0.1-0.2	5590
0.2-0.3	165
0.3-0.4	22
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