NPASS Compound

Natural Product: NPC475384

Natural Product ID	NPC475384
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Petrocortyne H
IUPAC Name	(3R,4E,14R,21Z,26E,43Z)-hexatetraconta-4,21,26,43-tetraen-1,12,15,45-tetrayne-3,14,28-triol
Synonyms	Petrocortyne H
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL504635
PubChem CID	10580326
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 119118 0 0 0 0 0 0 0 0999 V2000 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -10.3923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2500 -11.6913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -12.9904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7500 -14.2894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 -15.5885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2500 -16.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0000 -18.1865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7500 -19.4856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5000 -20.7846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7500 -22.0836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5000 -23.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2500 -24.6817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0000 -25.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.7500 -27.2798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0000 -28.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7500 -27.2798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2500 -27.2798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7500 -27.2798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.2500 -27.2798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2500 -28.7798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -30.0788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4510 -20.2356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2500 -3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5490 -0.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9510 -2.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7010 -3.3481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2990 -1.8481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0490 -3.1471 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4510 -4.6471 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2010 -5.9462 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7990 -4.4462 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5490 -5.7452 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9510 -7.2452 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7010 -8.5442 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2990 -7.0442 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0490 -8.3433 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4510 -9.8433 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2010 -11.1423 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7990 -9.6423 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5490 -10.9413 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9510 -12.4413 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7010 -13.7404 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2990 -12.2404 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0490 -13.5394 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4510 -15.0394 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2010 -16.3385 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7990 -14.8385 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5490 -16.1375 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9510 -17.6375 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7010 -18.9365 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2990 -17.4365 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0490 -18.7356 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0000 -20.7846 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6647 -22.2169 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2010 -24.1327 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7990 -22.6327 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.5490 -23.9317 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9510 -25.4317 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.2990 -25.2308 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8816 -26.4555 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.2500 -27.2798 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.7500 -29.8779 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3519 -27.3729 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5000 -30.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0000 -27.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0000 -30.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 -30.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 -27.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -30.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -27.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -27.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -27.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -30.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -30.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -27.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -27.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -30.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -30.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -27.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -27.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -30.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5000 -27.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5000 -30.0788 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7500 -29.8779 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0000 -25.9808 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2500 -25.7798 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.7500 -27.2798 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5490 -29.5298 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2010 -30.8288 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3177 -21.3209 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 3 0 2 3 1 0 3 4 2 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 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 3 0 32 33 1 0 33 34 1 0 34 35 3 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 1 0 45 46 3 0 44 47 1 0 33 48 1 0 19 49 1 0 1 50 1 0 3 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 9 61 1 0 9 62 1 0 10 63 1 0 10 64 1 0 11 65 1 0 11 66 1 0 12 67 1 0 12 68 1 0 13 69 1 0 13 70 1 0 14 71 1 0 14 72 1 0 15 73 1 0 15 74 1 0 16 75 1 0 16 76 1 0 17 77 1 0 17 78 1 0 18 79 1 0 18 80 1 0 19 81 1 0 20 82 1 0 21 83 1 0 22 84 1 0 22 85 1 0 23 86 1 0 23 87 1 0 24 88 1 0 24 89 1 0 25 90 1 0 26 91 1 0 27 92 1 0 27 93 1 0 28 94 1 0 28 95 1 0 29 96 1 0 29 97 1 0 30 98 1 0 30 99 1 0 33100 1 1 36101 1 0 36102 1 0 37103 1 0 37104 1 0 38105 1 0 38106 1 0 39107 1 0 39108 1 0 40109 1 0 40110 1 0 41111 1 0 41112 1 0 42113 1 0 43114 1 0 44115 1 6 46116 1 0 47117 1 0 48118 1 0 49119 1 0 M END

Standard InCHIKey	QGGNXNCVFAAWBQ-GCXPQEBYSA-N
Standard InCHI	InChI=1S/C46H70O3/c1-3-5-6-7-8-9-10-11-12-13-14-16-19-25-30-35-40-45(48)41-36-31-26-20-17-15-18-21-27-32-37-42-46(49)43-38-33-28-23-22-24-29-34-39-44(47)4-2/h1-2,5-6,15,17,34,36,39,41,44-49H,7-14,16,18-33,35,40H2/b6-5-,17-15-,39-34+,41-36+/t44-,45?,46-/m0/s1
SMILES	C#C/C=CCCCCCCCCCCCCCCC(/C=C/CCC/C=CCCCCC#C[C@@H](C#CCCCCCC/C=C/[C@H](C#C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	670.53	Volume:	798.905 ? Van der Waals volume.
Dense:	0.839	LogP:	9.186 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.973 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-9.168 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	31.0	Rigid Bonds:	8.0
TPSA:	60.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	3.0	Rings:	0.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.039	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.696	Fsp³:	0.652
MCE-18:	3.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.664	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.665	Promiscuous compounds:	0.033

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.049	MDCK Permeability:	-4.569
Pgp-inhibitor:	0.125	Pgp-substrate:	0.0
PAMPA:	0.0 ? 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%):	0.001	30% Bioavailability (F30%):	0.66
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	101.445%	Volume Distribution (VD):	0.616
Fu:	0.004% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.811	BCRP inhibitor:	0.999
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.046	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.508	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.962
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

3.833

Half-life (T1/2):

1.761

ADMET: Toxicity

hERG Blockers:	0.099	hERG Blockers (10um):	0.721
Human Hepatotoxicity (H-HT):	0.846	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.027	Rat Oral Acute Toxicity:	0.265
Maximum Recommended Daily Dose:	0.992	Skin Sensitization:	1.0
Carcinogencity:	0.067	Eye Corrosion:	0.087
Eye Irritation:	0.573	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.888
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.959
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.383
A549 Cytotoxicity:	0.479	Hek293 Cytotoxicity:	0.936
BCF:	-0.122 ? 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:	6.245 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	8.759 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.658 ? 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
NPO30927	Petrosia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514299]
NPO30927	Petrosia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21534590]
NPO30927	Petrosia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784165]

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
Inhibition	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT545	Individual protein	Phospholipase A2 group 1B	Homo sapiens	Inhibition	=	32.0	%	PubChem BioAssay data set

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 NPC475384 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	43672
0.1-0.2	5713
0.2-0.3	341
0.3-0.4	60
0.4-0.5	23
0.5-0.6	21
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	5
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473847
1.0	High Similarity	NPC473721
1.0	High Similarity	NPC473910
0.975	High Similarity	NPC473896
0.975	High Similarity	NPC473735
0.9512	High Similarity	NPC473725
0.85	High Similarity	NPC89824
0.85	High Similarity	NPC475477
0.85	High Similarity	NPC256656
0.85	High Similarity	NPC294278
0.85	High Similarity	NPC477723
0.7778	Intermediate Similarity	NPC473532
0.7556	Intermediate Similarity	NPC329608
0.7381	Intermediate Similarity	NPC197272
0.7209	Intermediate Similarity	NPC26102
0.7209	Intermediate Similarity	NPC477724
0.7083	Intermediate Similarity	NPC473652
0.6957	Remote Similarity	NPC224148
0.6957	Remote Similarity	NPC477725
0.6667	Remote Similarity	NPC168407
0.6429	Remote Similarity	NPC161838
0.617	Remote Similarity	NPC48058
0.6136	Remote Similarity	NPC187361
0.6047	Remote Similarity	NPC55383
0.5909	Remote Similarity	NPC471960
0.5909	Remote Similarity	NPC477727
0.56	Remote Similarity	NPC477726
0.5517	Remote Similarity	NPC594
0.5517	Remote Similarity	NPC48968
0.55	Remote Similarity	NPC607242
0.5273	Remote Similarity	NPC470967
0.5273	Remote Similarity	NPC470968
0.525	Remote Similarity	NPC170776
0.525	Remote Similarity	NPC9273
0.525	Remote Similarity	NPC165447
0.525	Remote Similarity	NPC471959
0.525	Remote Similarity	NPC199286
0.525	Remote Similarity	NPC489046
0.525	Remote Similarity	NPC76198
0.525	Remote Similarity	NPC610719
0.5192	Remote Similarity	NPC470969
0.5179	Remote Similarity	NPC601905
0.5179	Remote Similarity	NPC603973
0.5172	Remote Similarity	NPC475984
0.5094	Remote Similarity	NPC470965

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475384 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8723
0.1-0.2	411
0.2-0.3	16
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