NPASS Compound

Natural Product: NPC224148

Natural Product ID	NPC224148
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Petrotetrayndiol E
IUPAC Name	(3S,4E,14S,17E,21Z,27Z)-hexatetraconta-4,17,21,27-tetraen-1,12,15,45-tetrayne-3,14-diol
Synonyms	Petrotetrayndiol E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL449567
PubChem CID	10604337
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 3D 118117 0 0 0 0 0 0 0 0999 V2000 15.8453 -0.0631 -3.1545 C 0 0 0 0 0 0 0 0 0 0 0 0 16.1950 -0.0711 -2.0170 C 0 0 0 0 0 0 0 0 0 0 0 0 16.6199 -0.0783 -0.6577 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5309 -0.1833 0.3282 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5996 1.0315 0.4066 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6522 0.7559 1.5234 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6496 -0.3283 1.3040 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5759 0.1340 0.3507 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5326 -0.9695 0.1079 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3604 -0.3016 -0.6049 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2342 -1.2516 -0.8235 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9571 -0.5179 -1.2302 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6523 0.4770 -0.0959 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6244 -0.2545 1.2147 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5285 -1.2160 1.4537 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1555 -0.5973 1.6288 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1376 0.2493 2.8956 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7770 0.8185 3.1953 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2146 1.7761 2.2508 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1414 1.5416 1.4839 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4731 0.1928 1.5799 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5463 -0.4783 0.2102 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3308 0.1817 -0.8405 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7564 0.0285 -0.2886 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7090 0.2926 -1.3934 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4457 -0.8081 -1.8429 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1021 -2.0404 -1.1153 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1544 -2.7811 -0.3872 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0443 -2.0140 0.3950 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6078 -1.6056 1.4923 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7112 -0.6433 1.3173 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6850 0.2365 1.1630 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6997 1.1446 1.0047 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8983 1.4912 -0.4333 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0677 1.7806 -1.6035 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2480 2.1259 -3.0120 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3805 1.4781 -3.7128 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7359 1.7953 -3.2351 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1096 1.3267 -1.8485 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1272 -0.2079 -1.8056 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5256 -0.5606 -0.3941 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8767 -0.0328 -0.0600 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.8468 -0.9013 0.2787 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.1976 -0.4648 0.6146 C 0 0 1 0 0 0 0 0 0 0 0 0 -16.4674 -0.4776 2.1089 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.6787 -0.4926 3.2426 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.5747 0.7740 0.0862 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4202 2.4133 1.6206 O 0 0 0 0 0 0 0 0 0 0 0 0 15.5285 -0.0581 -4.2177 H 0 0 0 0 0 0 0 0 0 0 0 0 17.1395 0.9221 -0.4627 H 0 0 0 0 0 0 0 0 0 0 0 0 17.4044 -0.8895 -0.4828 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8558 -1.0427 -0.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8355 -0.5265 1.3660 H 0 0 0 0 0 0 0 0 0 0 0 0 15.1616 1.9530 0.6555 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1050 1.1791 -0.5738 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0237 1.7008 1.6748 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2090 0.5490 2.4658 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1932 -0.5379 2.3111 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0717 -1.2399 0.8777 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0319 0.9684 0.9092 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9584 0.5470 -0.5875 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2268 -1.2784 1.1108 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9652 -1.7932 -0.4549 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0557 0.5025 0.0917 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6736 0.2275 -1.5314 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0290 -1.9991 -0.0774 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4794 -1.8293 -1.7918 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1394 -1.1724 -1.4410 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1959 0.1236 -2.0847 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3164 1.3254 -0.1031 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6136 0.8158 -0.3215 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5920 0.4919 2.0254 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5963 -0.8106 1.4277 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4473 -1.8480 0.5493 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7967 -1.8967 2.3051 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8983 -0.0835 0.7409 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4451 -1.4573 1.7576 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8878 1.0876 2.7909 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4667 -0.3555 3.7533 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0899 0.0510 3.6014 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0016 1.4656 4.1484 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6887 2.7363 2.1585 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7699 2.2574 0.8148 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5778 0.4036 1.8539 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9175 -0.5032 2.2736 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6065 -0.3667 -0.0982 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2639 -1.5298 0.3779 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1027 1.2460 -0.9483 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2606 -0.3325 -1.8138 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9600 -0.7352 0.4061 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8283 0.9782 0.3904 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8450 1.2425 -1.8095 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1335 -0.6235 -2.6249 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0745 -2.0940 -0.6794 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9144 -2.7968 -2.0472 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8089 -3.3553 -1.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6786 -3.6489 0.1893 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5558 -1.2552 -0.5032 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2900 -1.9627 2.4141 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6601 0.7905 1.3493 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2757 2.1439 -3.5869 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5339 3.2409 -2.9865 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3367 1.7963 -4.7904 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2112 0.3542 -3.7845 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8565 2.9197 -3.2350 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5325 1.4186 -3.9543 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5237 1.7802 -1.0727 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1630 1.6494 -1.6549 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9210 -0.6122 -2.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1723 -0.6694 -2.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8105 -0.1910 0.3646 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5480 -1.6878 -0.2556 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.1414 1.0201 -0.0382 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.5980 -1.9761 0.3344 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.9110 -1.2473 0.2485 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.8734 -0.5088 4.3312 H 0 0 0 0 0 0 0 0 0 0 0 0 -17.5695 0.6895 -0.1086 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6149 2.7631 1.1067 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 3 0 2 3 1 0 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 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 2 0 20 21 1 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 2 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 1 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 6 56 1 0 6 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 9 63 1 0 10 64 1 0 10 65 1 0 11 66 1 0 11 67 1 0 12 68 1 0 12 69 1 0 13 70 1 0 13 71 1 0 14 72 1 0 14 73 1 0 15 74 1 0 15 75 1 0 16 76 1 0 16 77 1 0 17 78 1 0 17 79 1 0 18 80 1 0 18 81 1 0 19 82 1 0 20 83 1 0 21 84 1 0 21 85 1 0 22 86 1 0 22 87 1 0 23 88 1 0 23 89 1 0 24 90 1 0 24 91 1 0 25 92 1 0 26 93 1 0 27 94 1 0 27 95 1 0 28 96 1 0 28 97 1 0 29 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 M END

Standard InCHIKey	TXYZIRSIJCTANA-QPUIMWOUSA-N
Standard InCHI	InChI=1S/C46H70O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-34-37-40-43-46(48)44-41-38-35-32-31-33-36-39-42-45(47)4-2/h1-2,21-22,27-28,34,37,39,42,45-48H,5-20,23-26,29-33,35-36,38H2/b22-21-,28-27-,37-34+,42-39+/t45-,46-/m1/s1
SMILES	C#CCCCCCCCCCCCCCCCC/C=CCCCC/C=CCC/C=C/C#C[C@H](C#CCCCCCC/C=C/[C@@H](C#C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.54	Volume:	790.115 ? Van der Waals volume.
Dense:	0.828	LogP:	11.559 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.839 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-11.825 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	31.0	Rigid Bonds:	8.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.044	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.398	Fsp³:	0.652
MCE-18:	2.0 ? 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:	0.665	Fluc inhibitor:	0.009 ? 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:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.666	Promiscuous compounds:	0.108

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.026	MDCK Permeability:	-4.604
Pgp-inhibitor:	0.033	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%):	0.0	30% Bioavailability (F30%):	0.005
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	101.437%	Volume Distribution (VD):	0.583
Fu:	0.007% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	1.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.93	CYP2C9-substrate:	0.64
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.96	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.087 ? 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):

3.756

Half-life (T1/2):

2.139

ADMET: Toxicity

hERG Blockers:	0.032	hERG Blockers (10um):	0.682
Human Hepatotoxicity (H-HT):	0.603	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.146	Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.962	Skin Sensitization:	1.0
Carcinogencity:	0.093	Eye Corrosion:	0.351
Eye Irritation:	0.688	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.699
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.954
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.437
A549 Cytotoxicity:	0.421	Hek293 Cytotoxicity:	0.96
BCF:	-0.253 ? 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:	5.837 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	8.422 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.082 ? 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
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	(15-25 m depth) off Komun Island, Korea	1995-JUL	PMID[10217707]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346968]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170665]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754614]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesia	1996	PMID[18327911]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	Miyako sea-knoll, southwestern Japan (2525.64' N, 12542.48' E), at a depth of 415 m	2009-OCT	PMID[21534590]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	American Samoa	n.a.	PMID[23368996]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26821210]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917297]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
ED50	5
Inhibition	3

Activity Type	# Activity
Cell line	5
Organism	3

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
NPT81	Cell line	A549	Homo sapiens	ED50	=	24.5	ug ml-1	PMID[18242997]
NPT146	Cell line	SK-OV-3	Homo sapiens	ED50	=	1.7	ug ml-1	PMID[19933793]
NPT147	Cell line	SK-MEL-2	Homo sapiens	ED50	=	1.1	ug ml-1	PMID[16038541]
NPT574	Cell line	XF498	Homo sapiens	ED50	=	3.4	ug ml-1	PMID[12608857]
NPT148	Cell line	HCT-15	Homo sapiens	ED50	=	1.8	ug ml-1	PMID[22037378]
NPT6068	Organism	Simian virus 40	Simian virus 40	Inhibition	=	62.0	%	PMID[21214226]
NPT6068	Organism	Simian virus 40	Simian virus 40	Inhibition	=	83.0	%	PMID[25314129]
NPT6068	Organism	Simian virus 40	Simian virus 40	Inhibition	=	100.0	%	PMID[14664515]

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 NPC224148 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	44751
0.1-0.2	4681
0.2-0.3	295
0.3-0.4	62
0.4-0.5	20
0.5-0.6	24
0.6-0.7	14
0.7-0.8	0
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC329608
0.8	Intermediate Similarity	NPC89824
0.8	Intermediate Similarity	NPC475477
0.8	Intermediate Similarity	NPC256656
0.8	Intermediate Similarity	NPC294278
0.8	Intermediate Similarity	NPC477723
0.7255	Intermediate Similarity	NPC594
0.7255	Intermediate Similarity	NPC48968
0.7111	Intermediate Similarity	NPC473896
0.7111	Intermediate Similarity	NPC473735
0.6957	Remote Similarity	NPC473847
0.6957	Remote Similarity	NPC473721
0.6957	Remote Similarity	NPC473725
0.6957	Remote Similarity	NPC473910
0.6957	Remote Similarity	NPC475384
0.6957	Remote Similarity	NPC473532
0.6905	Remote Similarity	NPC197272
0.6667	Remote Similarity	NPC473652
0.6341	Remote Similarity	NPC55383
0.6275	Remote Similarity	NPC168407
0.619	Remote Similarity	NPC477727
0.6047	Remote Similarity	NPC187361
0.6	Remote Similarity	NPC26102
0.6	Remote Similarity	NPC477724
0.5745	Remote Similarity	NPC48058
0.5526	Remote Similarity	NPC170776
0.5526	Remote Similarity	NPC9273
0.5526	Remote Similarity	NPC165447
0.5526	Remote Similarity	NPC471959
0.5526	Remote Similarity	NPC199286
0.5526	Remote Similarity	NPC489046
0.5526	Remote Similarity	NPC76198
0.5526	Remote Similarity	NPC610719
0.551	Remote Similarity	NPC477725
0.5472	Remote Similarity	NPC470967
0.5472	Remote Similarity	NPC470968
0.5385	Remote Similarity	NPC607242
0.537	Remote Similarity	NPC601905
0.537	Remote Similarity	NPC603973
0.5283	Remote Similarity	NPC470964
0.5263	Remote Similarity	NPC125122
0.5263	Remote Similarity	NPC471276
0.5263	Remote Similarity	NPC471280
0.5263	Remote Similarity	NPC471281
0.52	Remote Similarity	NPC477726
0.5122	Remote Similarity	NPC474642
0.5122	Remote Similarity	NPC473913
0.5091	Remote Similarity	NPC474513

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC224148 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8779
0.1-0.2	363
0.2-0.3	8
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