NPASS Compound

Natural Product: NPC187376

Natural Product ID	NPC187376
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Trametenolic Acid
IUPAC Name	(2R)-2-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms	Trametenolic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL387689
PubChem CID	12309443
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 81 84 0 0 0 0 0 0 0 0999 V2000 7.0653 1.0356 0.8801 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9348 0.9762 1.8257 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0930 -0.0096 1.8364 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2042 -1.1482 0.8972 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8700 -1.2702 0.1587 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6167 -0.0272 -0.5838 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3263 0.0590 -1.3301 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1174 -1.0199 -2.3559 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8149 -1.6735 -1.8312 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0774 -0.4022 -1.5362 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0704 0.2927 -0.5958 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0020 -0.1789 0.8060 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6161 1.7409 -0.5990 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8286 1.8858 -0.3486 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6364 0.6439 -0.2958 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2004 -0.4946 -0.8774 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9328 -1.7740 -0.8723 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9699 -1.7759 0.2299 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7492 -0.4744 0.0251 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9442 0.7182 0.4152 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6476 0.8118 1.8757 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7442 1.9474 -0.0161 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1439 1.6335 -0.4215 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8652 0.6912 0.5173 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0979 -0.5906 0.6506 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8568 -1.6336 -0.1926 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0880 -1.1262 2.0574 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1285 1.3144 1.7316 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0804 0.3578 -2.8297 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6651 0.0692 -1.6814 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4769 -0.8523 -1.8877 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7263 1.2000 -2.4726 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7787 2.1018 2.7904 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6056 0.0459 0.8058 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6859 1.3191 -0.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8439 1.7614 1.2455 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2695 0.0016 2.5679 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0734 -1.1120 0.2547 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2300 -2.0690 1.5636 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0314 -2.1670 -0.4979 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1563 -1.5982 0.9076 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7516 0.8482 0.0391 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4613 1.0024 -1.9695 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9189 -1.7370 -2.4425 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8614 -0.6507 -3.3675 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0983 -2.2562 -0.9577 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3566 -2.3094 -2.5865 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1245 0.3373 1.3059 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8650 0.2709 1.3473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8248 -1.2354 0.9772 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9551 2.2813 -1.5111 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2224 2.2213 0.2291 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 2.5188 0.5543 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2498 2.5219 -1.1833 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4839 -1.8456 -1.8332 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2637 -2.6553 -0.8158 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6859 -2.6229 0.0929 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4854 -1.8368 1.2026 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9130 -0.4044 -1.0841 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0860 1.7509 2.0581 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5389 0.8765 2.5259 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0682 -0.0940 2.1721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7047 2.7442 0.7693 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2402 2.3824 -0.9028 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7235 2.5788 -0.4213 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1590 1.2184 -1.4555 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8817 0.5356 0.0467 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7217 -2.6514 0.2300 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5616 -1.5673 -1.2485 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9397 -1.4003 -0.1377 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7370 -2.0441 2.1800 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0856 -1.4532 2.4027 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5579 -0.3900 2.7745 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0468 1.6543 1.8134 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7432 1.0235 -3.0819 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0786 0.8384 -2.8526 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1395 -0.4207 -3.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4900 1.3558 -3.1175 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7357 2.2944 3.3427 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4527 3.0309 2.2737 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0241 1.8746 3.5745 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 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 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 24 28 1 0 10 29 1 6 6 30 1 0 30 31 2 0 30 32 1 0 2 33 1 0 11 7 1 0 20 15 1 0 16 10 1 0 25 19 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 6 42 1 1 7 43 1 6 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 12 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 18 58 1 0 19 59 1 6 21 60 1 0 21 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 24 67 1 6 26 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 32 78 1 0 33 79 1 0 33 80 1 0 33 81 1 0 M END

Standard InCHIKey	NBSBUIQBEPROBM-GIICLEHTSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,20-21,24-25,31H,8,10-18H2,1-7H3,(H,32,33)/t20-,21-,24+,25+,28-,29-,30+/m1/s1
SMILES	CC(=CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	511.671 ? Van der Waals volume.
Dense:	0.892	LogP:	4.379 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.423 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.192 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.42	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.708	Fsp³:	0.833
MCE-18:	81.455 ? 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:	0.919	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.019 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.571	Promiscuous compounds:	0.192

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.268	MDCK Permeability:	-4.917
Pgp-inhibitor:	0.003	Pgp-substrate:	0.098
PAMPA:	0.999 ? 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%):	0.214	30% Bioavailability (F30%):	0.009
50% Bioavailability (F50%):	0.885

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.49	MRP1:	0.992
Plasma Protein Binding (PPB):	91.127%	Volume Distribution (VD):	-0.302
Fu:	5.977% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.952	BCRP inhibitor:	0.021
BSEP inhibitor:	0.651

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.23	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.023	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.075	CYP3A4-substrate:	0.785
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.006
HLM stability:	0.0 ? 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):

8.407

Half-life (T1/2):

0.558

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.055
Human Hepatotoxicity (H-HT):	0.598	Drug-induced Liver Injury (DILI):	0.212
AMES Toxicity:	0.206	Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.12	Skin Sensitization:	0.998
Carcinogencity:	0.721	Eye Corrosion:	0.487
Eye Irritation:	0.935	Respiratory Toxicity:	0.767
Drug-induced Neurotoxicity:	0.017	Ototoxicity:	0.572
Hematotoxicity:	0.576	Drug-induced Nephrotoxicity:	0.937
Genotoxicity:	0.042	RPMI-8226 Immunitoxicity:	0.05
A549 Cytotoxicity:	0.095	Hek293 Cytotoxicity:	0.068
BCF:	1.805 ? 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:	4.544 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.825 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.324 ? 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
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785428]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[10785428]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[17049251]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[18387711]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[21939217]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24359303]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584403]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13025	Senecio lanceus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9732	Glochidion heyneanum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11286	Helichrysum bilobum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11286	Helichrysum bilobum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13025	Senecio lanceus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9732	Glochidion heyneanum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	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	3
Activity	2
Inhibition	5
ED50	4
Survival	1

Activity Type	# Activity
Individual protein	1
Cell line	6
Organism	4
Unchecked	2
Non-molecular	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT526	Individual protein	Alpha-glucosidase MAL62	Saccharomyces cerevisiae	IC50	=	17090.0	nM	DOI[10.1007/s00044-011-9741-y]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[17049251]
NPT550	Cell line	T-24	Homo sapiens	ED50	=	4.4	ug ml-1	PMID[10785428]
NPT2428	Cell line	HT-3	Homo sapiens	ED50	=	3.5	ug ml-1	PMID[10785428]
NPT2245	Cell line	SiHa	Homo sapiens	ED50	=	5.5	ug ml-1	PMID[10785428]
NPT2306	Cell line	Ca-Ski	Homo sapiens	ED50	=	6.2	ug ml-1	PMID[10785428]
NPT137	Cell line	L1210	Mus musculus	IC50	=	62500.0	nM	PMID[23092389]
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	102.3	nM	PMID[37847948]
NPT28438	Unchecked	Unchecked	n.a.	Activity	=	75.0	%	PMID[29353722]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	75.0	%	PMID[24359303]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	9.2	%	PMID[17049251]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	45.0	%	PMID[17049251]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	75.4	%	PMID[17049251]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	98.6	%	PMID[17049251]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Survival	=	92.0	%	PMID[24359303]

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 NPC187376 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	20302
0.1-0.2	25106
0.2-0.3	3945
0.3-0.4	375
0.4-0.5	79
0.5-0.6	23
0.6-0.7	15
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233836
1.0	High Similarity	NPC159046
0.7833	Intermediate Similarity	NPC55309
0.7833	Intermediate Similarity	NPC28252
0.7705	Intermediate Similarity	NPC469400
0.7581	Intermediate Similarity	NPC76895
0.7581	Intermediate Similarity	NPC173272
0.75	Intermediate Similarity	NPC482518
0.6818	Remote Similarity	NPC148414
0.6818	Remote Similarity	NPC111585
0.6818	Remote Similarity	NPC175628
0.6769	Remote Similarity	NPC84271
0.6769	Remote Similarity	NPC102414
0.6719	Remote Similarity	NPC201912
0.6719	Remote Similarity	NPC38350
0.6719	Remote Similarity	NPC601139
0.6418	Remote Similarity	NPC142361
0.6418	Remote Similarity	NPC474684
0.629	Remote Similarity	NPC46160
0.629	Remote Similarity	NPC202642
0.6154	Remote Similarity	NPC94755
0.6094	Remote Similarity	NPC214570
0.6	Remote Similarity	NPC469406
0.5882	Remote Similarity	NPC482908
0.5882	Remote Similarity	NPC48330
0.5882	Remote Similarity	NPC484974
0.5882	Remote Similarity	NPC23434
0.5781	Remote Similarity	NPC275910
0.5714	Remote Similarity	NPC289213
0.5634	Remote Similarity	NPC484976
0.5634	Remote Similarity	NPC77168
0.5556	Remote Similarity	NPC475921
0.5556	Remote Similarity	NPC474704
0.5352	Remote Similarity	NPC222845
0.5352	Remote Similarity	NPC296577
0.5278	Remote Similarity	NPC474889
0.5231	Remote Similarity	NPC606082
0.5224	Remote Similarity	NPC231477
0.5224	Remote Similarity	NPC87489
0.5224	Remote Similarity	NPC123724
0.5211	Remote Similarity	NPC486193
0.5152	Remote Similarity	NPC118508
0.5152	Remote Similarity	NPC484086
0.5147	Remote Similarity	NPC132635
0.5147	Remote Similarity	NPC601223
0.5072	Remote Similarity	NPC471724

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC187376 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6374
0.1-0.2	2686
0.2-0.3	87
0.3-0.4	3
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