NPASS Compound

Natural Product: NPC105222

Natural Product ID	NPC105222
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PJHBZROILRCFRB-RBZGWYANSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10697375
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 75 78 0 0 0 0 0 0 0 0999 V2000 2.0427 -1.6215 1.6452 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4587 -0.8204 0.7609 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5079 0.6504 0.9837 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7643 1.0018 2.4186 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2968 2.3984 2.7751 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1879 2.5436 2.7285 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8170 1.3439 2.1297 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8622 1.3877 1.3504 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4438 2.7601 1.0910 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4009 0.3311 0.5521 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4598 0.4973 -0.0833 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7335 -1.0639 0.3946 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7029 -1.9429 -0.3538 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1506 -2.1881 -1.7402 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5236 -3.5110 -1.9268 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3305 -0.9806 -1.8778 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6088 -0.7671 -0.5363 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7109 -1.3172 -0.4356 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6023 -0.9467 -1.5001 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3259 -1.9493 -2.1273 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1657 -3.1319 -1.7440 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2759 -1.6978 -3.2196 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6615 -0.6671 -3.0007 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7959 0.3671 -3.8731 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 1.1420 -3.5414 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0247 0.6081 -5.0683 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2370 1.7538 -5.8297 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4881 1.9902 -6.9840 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4456 1.1015 -7.4215 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6341 0.0034 -6.6733 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9422 -0.2436 -5.5531 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4463 -1.3843 1.6424 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9758 -2.4423 2.3107 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7382 -3.4363 1.6060 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7237 -2.5247 3.7691 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4830 2.5657 4.0272 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4852 1.4025 4.9904 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5584 3.9204 4.7468 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5555 -1.2650 2.5237 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0136 -2.6957 1.4923 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4850 0.9254 0.3742 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7944 1.2787 0.5280 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4464 0.2771 3.1628 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8915 1.0435 2.5428 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9513 3.2135 2.5061 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5303 3.5220 2.3214 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3821 0.3707 2.4117 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7280 3.2111 2.0837 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3019 2.7264 0.3978 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7029 3.4422 0.6546 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6434 -1.3762 -0.4819 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9748 -2.8657 0.1740 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9903 -2.1151 -2.5016 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7743 -3.4832 -2.7773 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1019 -3.9926 -1.0378 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2892 -4.2144 -2.3216 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1105 -0.1708 -1.8122 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4344 0.3828 -0.5985 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7291 -2.4355 -0.3203 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3338 -1.8536 -2.9264 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1795 -0.6324 -3.5711 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0642 -2.3317 -4.1030 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0011 2.4477 -5.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2873 2.8945 -7.5416 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9913 1.3187 -8.3231 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1396 -1.1507 -5.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6381 -2.3274 4.3673 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0757 -1.7680 3.9846 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3014 -3.5031 4.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0931 0.5334 4.6422 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2057 1.7198 6.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5532 1.0585 5.0511 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5296 4.0261 5.2691 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3167 3.9649 5.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4172 4.6918 3.9627 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 8 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 16 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 12 32 1 1 32 33 1 0 33 34 2 0 33 35 1 0 6 36 1 0 36 37 1 0 36 38 1 0 18 2 1 0 31 26 1 0 36 5 1 0 17 12 1 0 1 39 1 0 1 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 6 6 46 1 6 7 47 1 0 9 48 1 0 9 49 1 0 9 50 1 0 13 51 1 0 13 52 1 0 14 53 1 6 15 54 1 0 15 55 1 0 15 56 1 0 16 57 1 1 17 58 1 6 18 59 1 1 22 60 1 0 22 61 1 0 22 62 1 0 27 63 1 0 28 64 1 0 29 65 1 0 31 66 1 0 35 67 1 0 35 68 1 0 35 69 1 0 37 70 1 0 37 71 1 0 37 72 1 0 38 73 1 0 38 74 1 0 38 75 1 0 M END

Standard InCHIKey	PJHBZROILRCFRB-RBZGWYANSA-N
Standard InCHI	InChI=1S/C30H37NO7/c1-16-10-11-22-23(29(22,6)7)13-17(2)27(34)30(38-20(5)33)14-18(3)26(24(30)25(16)36-19(4)32)37-28(35)21-9-8-12-31-15-21/h8-9,12-13,15,18,22-26H,1,10-11,14H2,2-7H3/b17-13+/t18-,22-,23+,24-,25-,26-,30+/m0/s1
SMILES	C=C1CC[C@H]2[C@@H](/C=C(C)/C(=O)[C@]3(C[C@H](C)[C@@H]([C@@H]3[C@H]1OC(=O)C)OC(=O)c1cccnc1)OC(=O)C)C2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	523.26	Volume:	542.01 ? Van der Waals volume.
Dense:	0.965	LogP:	3.296 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.213 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.521 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	28.0
TPSA:	108.86 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.319	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.283	Fsp³:	0.567
MCE-18:	107.511 ? 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:	0.516	Fluc inhibitor:	0.015 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.02 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.022	Promiscuous compounds:	0.093

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.268	MDCK Permeability:	-4.937
Pgp-inhibitor:	0.975	Pgp-substrate:	0.029
PAMPA:	0.182 ? 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%):	0.4	30% Bioavailability (F30%):	0.515
50% Bioavailability (F50%):	0.862

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.997
Plasma Protein Binding (PPB):	85.138%	Volume Distribution (VD):	0.229
Fu:	16.127% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.924	BCRP inhibitor:	0.019
BSEP inhibitor:	0.976

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.008
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.657
CYP3A4-inhibitor:	0.491	CYP3A4-substrate:	0.633
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

5.569

Half-life (T1/2):

0.55

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.081
Human Hepatotoxicity (H-HT):	0.469	Drug-induced Liver Injury (DILI):	0.934
AMES Toxicity:	0.411	Rat Oral Acute Toxicity:	0.271
Maximum Recommended Daily Dose:	0.375	Skin Sensitization:	0.991
Carcinogencity:	0.816	Eye Corrosion:	0.0
Eye Irritation:	0.617	Respiratory Toxicity:	0.14
Drug-induced Neurotoxicity:	0.119	Ototoxicity:	0.298
Hematotoxicity:	0.649	Drug-induced Nephrotoxicity:	0.82
Genotoxicity:	0.976	RPMI-8226 Immunitoxicity:	0.182
A549 Cytotoxicity:	0.159	Hek293 Cytotoxicity:	0.36
BCF:	1.21 ? 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:	4.118 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.743 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.356 ? 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
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542364]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15165157]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[21627109]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21627109]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30817151]
NPO8283	Pseudophegopteris subaurita	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10733	Plantago uniflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10479	Ophiocoma echinata	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10959	Kalanchoe marmorata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5571	Jacobaea arnautorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3940	Erioderma chilense	Species	Pannariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4494	Ecbolium linneanum	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10833	Heteromma simplicifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1000	Thymus transcaucasicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1000	Thymus transcaucasicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10833	Heteromma simplicifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5571	Jacobaea arnautorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4494	Ecbolium linneanum	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8283	Pseudophegopteris subaurita	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10733	Plantago uniflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10479	Ophiocoma echinata	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3940	Erioderma chilense	Species	Pannariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10959	Kalanchoe marmorata	Species	Crassulaceae	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
Activity	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
NPT2615	Cell line	HEK-293T	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[34267886]

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 NPC105222 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	12712
0.1-0.2	35222
0.2-0.3	1686
0.3-0.4	179
0.4-0.5	44
0.5-0.6	11
0.6-0.7	2
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
0.8	Intermediate Similarity	NPC482351
0.7467	Intermediate Similarity	NPC42234
0.6957	Remote Similarity	NPC37784
0.6067	Remote Similarity	NPC482353
0.5833	Remote Similarity	NPC276652
0.5747	Remote Similarity	NPC482263
0.5698	Remote Similarity	NPC482347
0.5556	Remote Similarity	NPC317191
0.5517	Remote Similarity	NPC270364
0.5517	Remote Similarity	NPC118799
0.5495	Remote Similarity	NPC470190
0.5319	Remote Similarity	NPC482258
0.5104	Remote Similarity	NPC187494
0.5056	Remote Similarity	NPC3450
0.5056	Remote Similarity	NPC122504

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC105222 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3985
0.1-0.2	5068
0.2-0.3	92
0.3-0.4	5
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