NPASS Compound

Natural Product: NPC57526

Natural Product ID	NPC57526
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XQCDLUKPQQDOBO-VEHNERKYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101630930
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003060] 16-oxosteroids

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 81 0 0 0 0 0 0 0 0999 V2000 4.8011 0.5365 2.7728 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7814 0.5451 1.2136 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1124 2.0235 0.9174 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4001 0.1958 0.8327 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0338 -1.1575 1.4616 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6502 -1.6002 1.2555 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8981 -1.0843 0.0762 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6549 -2.1405 -1.0117 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4776 0.1374 -0.5424 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8098 0.5397 -1.7975 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6471 0.8187 -1.5522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2751 -0.0414 -0.5108 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5887 -0.1509 -0.5367 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4431 0.5662 -1.5701 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5731 1.3083 -0.8390 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9788 2.3584 0.0728 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3697 2.0228 -1.9079 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4109 0.3433 -0.0798 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5317 -0.2747 0.9971 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3732 -1.0066 0.4223 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9630 -2.1736 -0.3928 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5597 -1.6172 1.4987 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1797 -2.0203 1.0181 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5180 -0.7364 0.5466 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4562 0.1370 1.7828 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9934 0.0900 -0.5776 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4965 -1.2703 -1.0759 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4821 1.0263 -1.6064 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9305 1.0555 -1.8684 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3672 1.8637 -2.6653 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6523 1.1946 3.0372 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8896 0.9656 3.1742 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0789 -0.4691 3.1475 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5835 -0.1354 0.9398 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0927 2.1437 0.4376 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2685 2.5518 0.4400 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2381 2.6058 1.8913 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7390 0.9318 1.3596 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8412 -1.8617 1.2131 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2255 -0.9573 2.5666 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6334 -2.7267 1.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0778 -1.4046 2.2148 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9152 -3.1523 -0.6656 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4150 -2.0979 -1.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2141 -1.9445 -1.9418 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2541 0.9969 0.1626 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9915 -0.0960 -2.6829 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2362 1.5451 -2.1080 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 1.8746 -1.3001 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1245 0.6672 -2.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8804 -0.1559 -2.2529 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8880 1.3983 -2.0508 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6179 3.2455 -0.5100 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1409 1.9691 0.6772 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7294 2.7414 0.7831 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6721 2.6479 -2.4938 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1218 2.6500 -1.3610 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8979 1.2614 -2.4930 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8357 -0.4186 -0.7377 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2203 0.8781 0.4812 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1302 -0.9743 1.5959 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1844 0.5326 1.6806 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6359 -2.7797 0.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0598 -2.7790 -0.7027 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4926 -1.8296 -1.2811 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5397 -1.0221 2.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0515 -2.5894 1.8022 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2811 -2.7996 0.2812 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6469 -2.4083 1.8829 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4585 0.6929 1.9282 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6392 -0.4444 2.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3201 0.8664 1.7703 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5990 -1.2546 -0.8143 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0962 -2.1345 -0.5934 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5060 -1.3138 -2.1955 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0436 0.6371 -2.5834 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0808 2.0607 -1.5362 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6393 0.3966 -1.3929 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 9 26 1 0 26 27 1 6 26 28 1 0 28 29 1 0 29 30 2 0 26 4 1 0 24 7 1 0 24 12 1 0 20 13 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 3 35 1 0 3 36 1 0 3 37 1 0 4 38 1 1 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 8 43 1 0 8 44 1 0 8 45 1 0 9 46 1 1 10 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 14 51 1 0 14 52 1 0 16 53 1 0 16 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 17 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 21 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 25 70 1 0 25 71 1 0 25 72 1 0 27 73 1 0 27 74 1 0 27 75 1 0 28 76 1 0 28 77 1 0 29 78 1 0 M END

Standard InCHIKey	XQCDLUKPQQDOBO-VEHNERKYSA-N
Standard InCHI	InChI=1S/C29H48O/c1-20(2)21-11-12-29(8)24(27(21,6)17-18-30)10-9-22-23-19-25(3,4)13-14-26(23,5)15-16-28(22,29)7/h18,20-21,24H,9-17,19H2,1-8H3/t21-,24+,26+,27-,28+,29+/m0/s1
SMILES	CC(C)[C@@H]1CC[C@]2(C)[C@H](CCC3=C4CC(C)(C)CC[C@]4(C)CC[C@@]23C)[C@@]1(C)CC=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.37	Volume:	479.432 ? Van der Waals volume.
Dense:	0.86	LogP:	6.032 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.246 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.838 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	22.0
TPSA:	17.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.336	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.773	Fsp³:	0.897
MCE-18:	82.618 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.919	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.925	Promiscuous compounds:	0.037

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.751	MDCK Permeability:	-4.749
Pgp-inhibitor:	0.999	Pgp-substrate:	0.002
PAMPA:	0.241 ? 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%):	0.38	30% Bioavailability (F30%):	0.111
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.887	MRP1:	0.91
Plasma Protein Binding (PPB):	98.473%	Volume Distribution (VD):	0.715
Fu:	2.45% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.243
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.949	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.588
CYP2C9-inhibitor:	0.054	CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.028	CYP2D6-substrate:	0.783
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.129	CYP2C8-inhibitor:	0.999
HLM stability:	1.0 ? 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):

8.675

Half-life (T1/2):

0.089

ADMET: Toxicity

hERG Blockers:	0.076	hERG Blockers (10um):	0.297
Human Hepatotoxicity (H-HT):	0.606	Drug-induced Liver Injury (DILI):	0.267
AMES Toxicity:	0.393	Rat Oral Acute Toxicity:	0.454
Maximum Recommended Daily Dose:	0.616	Skin Sensitization:	0.982
Carcinogencity:	0.831	Eye Corrosion:	0.322
Eye Irritation:	0.822	Respiratory Toxicity:	0.712
Drug-induced Neurotoxicity:	0.342	Ototoxicity:	0.376
Hematotoxicity:	0.432	Drug-induced Nephrotoxicity:	0.881
Genotoxicity:	0.287	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.205	Hek293 Cytotoxicity:	0.406
BCF:	2.856 ? 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:	5.194 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.251 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.309 ? 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
NPO17048	Jungermannia subulata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11999396]
NPO7166	Streptomyces aureus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2066	Streptomyces ipomoeae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17168	Ageratina riparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16027	Niphogeton ternata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15580	Justicia simplex	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO426	Camellia reticulata	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17488	Rhoiptelea chiliantha	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17048	Jungermannia subulata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18903	Chromodoris willani	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18434	Dactylosporangium aurantiacum	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17264	Mycena haematopus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16027	Niphogeton ternata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15580	Justicia simplex	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16027	Niphogeton ternata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15580	Justicia simplex	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO426	Camellia reticulata	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18434	Dactylosporangium aurantiacum	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16942	Asparagus thunbergianus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11999	Piptadenia peregrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16027	Niphogeton ternata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5062	Aristolochia tagala	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7166	Streptomyces aureus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15832	Ruscus hypophyllum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13892	Calea clausseniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16631	Libocedrus yateensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15580	Justicia simplex	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18044	Lotus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17933	Cylicodaphne sebifera	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17488	Rhoiptelea chiliantha	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17048	Jungermannia subulata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18903	Chromodoris willani	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17264	Mycena haematopus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17168	Ageratina riparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2066	Streptomyces ipomoeae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16421	Chalciporus piperatus	Species	Boletaceae	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

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

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 NPC57526 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	30238
0.1-0.2	18308
0.2-0.3	1292
0.3-0.4	20
0.4-0.5	0
0.5-0.6	1
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	Natural Product ID
0.569	Remote Similarity	NPC89294

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC57526 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7852
0.1-0.2	1270
0.2-0.3	28
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