NPASS Compound

Natural Product: NPC244757

Natural Product ID	NPC244757
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UXQHEFSCBHNPKK-JECBATMWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 115122 0 0 0 0 0 0 0 0999 V2000 -10.4900 0.7020 -2.2048 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7454 1.8532 -1.5558 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1949 1.3516 -0.2385 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8142 1.9008 -0.0604 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8601 1.4470 -1.1343 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3541 0.0720 -0.7565 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1617 -0.9507 -1.5259 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9564 0.0521 -1.3253 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7284 1.4743 -1.7741 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3365 1.8777 -1.2632 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7254 0.5521 -0.9388 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5282 0.5877 -0.0514 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3351 0.9250 -0.9638 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9083 0.3233 -0.3478 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8425 0.3981 1.1785 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1846 0.2174 1.7865 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5812 -1.2215 1.9599 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5300 -1.8271 2.9028 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2546 -1.8660 2.1032 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2389 -0.5039 1.7061 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8842 0.1235 2.9041 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2336 -0.7122 0.5918 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4274 -1.4785 1.0749 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5297 -1.5297 0.0263 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9011 -0.1222 -0.2608 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2767 0.5875 1.0183 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8480 -1.3450 2.4822 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7172 -2.0589 1.7036 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9223 -1.2382 1.3889 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1500 -2.0937 1.7021 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9700 -3.3948 0.9521 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7903 -4.1002 1.5899 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9871 -4.7875 0.5320 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0360 -3.2409 2.3769 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1560 -4.1309 1.1511 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3351 -1.4542 1.4551 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9666 -0.8661 0.0520 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1813 0.4821 -0.1493 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4721 0.6984 -0.8566 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1563 1.3058 -2.2319 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5121 2.6435 -1.9232 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3560 2.4787 -0.9581 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1531 3.2641 -1.3914 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1716 3.2633 -0.4277 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0893 1.1420 -0.6951 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5107 3.4705 -1.4039 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2340 0.4834 -2.8394 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2767 1.5604 -0.1196 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7294 2.2557 -1.2339 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5087 1.4619 -2.3463 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5830 2.3176 -2.3899 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2638 0.6052 -3.2711 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1944 -0.2750 -1.7201 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5869 0.7925 -1.9854 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4276 2.7142 -1.3447 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1253 0.2447 -0.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8108 1.7064 0.6062 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8327 3.0240 -0.0078 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4662 1.5797 0.9468 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4115 -0.1453 0.3086 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8513 -0.4971 -2.2571 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7285 -1.6165 -0.8384 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5011 -1.6341 -2.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8295 -0.6901 -2.1140 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6752 1.4946 -2.8734 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8018 2.4801 -1.9952 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4800 2.4976 -0.3554 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4876 0.0318 -1.8822 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5508 1.4243 0.6873 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1821 2.0236 -0.9954 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4982 0.5070 -1.9773 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1062 -0.7142 -0.6851 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8044 0.9032 -0.6492 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5087 1.4518 1.3980 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2387 0.7559 2.7624 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9341 0.6712 1.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4433 -1.7157 0.9898 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7949 -2.8554 3.1900 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3555 -1.1606 3.7716 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4052 -2.5350 1.2492 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5255 -2.3413 2.7440 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4440 1.0372 2.7044 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0520 0.3784 3.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5288 -0.5891 3.4808 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7569 -1.3694 -0.1965 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8438 -1.1139 2.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1098 -2.5279 1.2463 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1676 -2.0645 -0.8527 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3781 -2.0757 0.4491 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6319 -0.1893 1.7313 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0947 1.3356 0.8423 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4373 1.1678 1.4037 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1688 -2.3575 0.7632 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0444 -0.3187 1.9993 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0316 -2.3591 2.7930 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7441 -3.2571 -0.1140 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2075 -4.8751 2.2652 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9194 -4.9301 0.8442 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3971 -5.8083 0.3891 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0558 -4.2928 -0.4591 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4008 -4.6372 0.3599 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0393 -1.8432 2.0260 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2784 0.9189 0.8894 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9811 -0.2864 -0.9910 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0672 1.4895 -2.8078 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1370 3.0865 -2.8534 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6967 2.9244 0.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7742 2.9738 -2.3908 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5064 4.3293 -1.5002 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2765 3.4191 -0.8158 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2077 3.5379 -2.0980 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6018 -0.1407 -3.4975 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9918 1.5711 0.8497 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3053 3.3374 -2.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8876 2.4511 -3.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 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 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 17 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 31 35 1 0 30 36 1 0 29 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 1 0 43 44 1 0 42 45 1 0 41 46 1 0 40 47 1 0 39 48 1 0 9 49 1 0 5 50 1 6 50 51 1 0 51 2 1 0 49 5 1 0 25 8 1 0 34 28 1 0 45 38 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 1 3 56 1 0 3 57 1 0 4 58 1 0 4 59 1 0 6 60 1 1 7 61 1 0 7 62 1 0 7 63 1 0 8 64 1 6 9 65 1 6 10 66 1 0 10 67 1 0 11 68 1 6 12 69 1 1 13 70 1 0 13 71 1 0 14 72 1 0 14 73 1 0 15 74 1 6 16 75 1 0 16 76 1 0 17 77 1 6 18 78 1 0 18 79 1 0 19 80 1 0 19 81 1 0 21 82 1 0 21 83 1 0 21 84 1 0 22 85 1 6 23 86 1 0 23 87 1 0 24 88 1 0 24 89 1 0 26 90 1 0 26 91 1 0 26 92 1 0 28 93 1 6 29 94 1 1 30 95 1 1 31 96 1 6 32 97 1 1 33 98 1 0 33 99 1 0 33100 1 0 35101 1 0 36102 1 0 38103 1 1 39104 1 6 40105 1 6 41106 1 6 42107 1 1 43108 1 0 43109 1 0 44110 1 0 46111 1 0 47112 1 0 48113 1 0 51114 1 0 51115 1 0 M END

Standard InCHIKey	UXQHEFSCBHNPKK-JECBATMWSA-N
Standard InCHI	InChI=1S/C39H64O12/c1-18-8-13-39(46-17-18)19(2)28-26(51-39)15-25-23-7-6-21-14-22(9-11-37(21,4)24(23)10-12-38(25,28)5)48-36-34(32(44)29(41)20(3)47-36)50-35-33(45)31(43)30(42)27(16-40)49-35/h18-36,40-45H,6-17H2,1-5H3/t18-,19-,20-,21+,22-,23+,24-,25-,26-,27+,28-,29-,30+,31-,32+,33+,34+,35-,36-,37-,38-,39+/m0/s1
SMILES	C[C@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC[C@@H]6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	724.44	Volume:	720.131 ? Van der Waals volume.
Dense:	1.006	LogP:	3.247 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.697 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.939 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	42.0
TPSA:	176.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	8.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.229	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.19	Fsp³:	1.0
MCE-18:	200.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.757	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.031 ? 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:	0.243	Promiscuous compounds:	0.033

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.886	MDCK Permeability:	-5.033
Pgp-inhibitor:	0.03	Pgp-substrate:	0.479
PAMPA:	0.956 ? 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%):	0.008	30% Bioavailability (F30%):	0.407
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.03
Plasma Protein Binding (PPB):	68.208%	Volume Distribution (VD):	-0.345
Fu:	28.192% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.206
BSEP inhibitor:	0.95

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.531
HLM stability:	0.001 ? 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):

1.518

Half-life (T1/2):

3.051

ADMET: Toxicity

hERG Blockers:	0.053	hERG Blockers (10um):	0.259
Human Hepatotoxicity (H-HT):	0.599	Drug-induced Liver Injury (DILI):	0.959
AMES Toxicity:	0.727	Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.111	Skin Sensitization:	1.0
Carcinogencity:	0.214	Eye Corrosion:	0.0
Eye Irritation:	0.014	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.983
Hematotoxicity:	0.217	Drug-induced Nephrotoxicity:	0.588
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.171
A549 Cytotoxicity:	0.628	Hek293 Cytotoxicity:	0.773
BCF:	2.115 ? 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:	3.599 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.672 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.214 ? 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
NPO11520	Homalanthus acuminatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11520	Homalanthus acuminatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2470	Abies spectabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11520	Homalanthus acuminatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10817	Perilla ocymoides	Species	Araneidae	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 NPC244757 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	27544
0.1-0.2	18890
0.2-0.3	2597
0.3-0.4	557
0.4-0.5	137
0.5-0.6	59
0.6-0.7	48
0.7-0.8	1
0.8-0.85	3
0.85-0.9	1
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC477451
0.9351	High Similarity	NPC297348
0.9351	High Similarity	NPC249204
0.9351	High Similarity	NPC48339
0.9351	High Similarity	NPC141769
0.9351	High Similarity	NPC477547
0.878	High Similarity	NPC211354
0.8471	Intermediate Similarity	NPC6295
0.8353	Intermediate Similarity	NPC107962
0.8118	Intermediate Similarity	NPC19400
0.7865	Intermediate Similarity	NPC160426
0.7857	Intermediate Similarity	NPC234352
0.7791	Intermediate Similarity	NPC206003
0.7791	Intermediate Similarity	NPC473610
0.7738	Intermediate Similarity	NPC325828
0.7674	Intermediate Similarity	NPC222731
0.7647	Intermediate Similarity	NPC294686
0.7473	Intermediate Similarity	NPC113044
0.7473	Intermediate Similarity	NPC283829
0.7473	Intermediate Similarity	NPC161676
0.7368	Intermediate Similarity	NPC128572
0.7303	Intermediate Similarity	NPC107188
0.7294	Intermediate Similarity	NPC485594
0.7204	Intermediate Similarity	NPC475351
0.7083	Intermediate Similarity	NPC471464
0.7065	Intermediate Similarity	NPC485595
0.7053	Intermediate Similarity	NPC475643
0.6989	Remote Similarity	NPC141433
0.6989	Remote Similarity	NPC195297
0.6979	Remote Similarity	NPC92890
0.6932	Remote Similarity	NPC177834
0.69	Remote Similarity	NPC475625
0.6837	Remote Similarity	NPC480555
0.6837	Remote Similarity	NPC150372
0.6768	Remote Similarity	NPC184617
0.6703	Remote Similarity	NPC250393
0.6703	Remote Similarity	NPC474399
0.6702	Remote Similarity	NPC125324
0.6633	Remote Similarity	NPC477809
0.6629	Remote Similarity	NPC181845
0.66	Remote Similarity	NPC97700
0.66	Remote Similarity	NPC30856
0.6559	Remote Similarity	NPC306131
0.6559	Remote Similarity	NPC54619
0.6559	Remote Similarity	NPC200802
0.6531	Remote Similarity	NPC470433
0.6531	Remote Similarity	NPC46190
0.6531	Remote Similarity	NPC171073
0.6484	Remote Similarity	NPC291203
0.6484	Remote Similarity	NPC217205
0.6477	Remote Similarity	NPC24960
0.6476	Remote Similarity	NPC480553
0.64	Remote Similarity	NPC300557
0.6321	Remote Similarity	NPC132080
0.6286	Remote Similarity	NPC480554
0.6238	Remote Similarity	NPC51172
0.6238	Remote Similarity	NPC49032
0.6224	Remote Similarity	NPC14704
0.62	Remote Similarity	NPC602423
0.618	Remote Similarity	NPC473774
0.618	Remote Similarity	NPC481419
0.618	Remote Similarity	NPC481417
0.6154	Remote Similarity	NPC269297
0.6154	Remote Similarity	NPC222202
0.6136	Remote Similarity	NPC277715
0.6105	Remote Similarity	NPC128123
0.6095	Remote Similarity	NPC475333
0.6095	Remote Similarity	NPC224098
0.6095	Remote Similarity	NPC208383
0.6058	Remote Similarity	NPC475319
0.6038	Remote Similarity	NPC194207
0.6038	Remote Similarity	NPC232037
0.6038	Remote Similarity	NPC22779
0.602	Remote Similarity	NPC470432
0.602	Remote Similarity	NPC230507
0.5981	Remote Similarity	NPC470864
0.598	Remote Similarity	NPC248746
0.5943	Remote Similarity	NPC116756
0.5941	Remote Similarity	NPC473601
0.5926	Remote Similarity	NPC83137
0.59	Remote Similarity	NPC305423
0.5893	Remote Similarity	NPC480556
0.5843	Remote Similarity	NPC144790
0.5843	Remote Similarity	NPC149400
0.5824	Remote Similarity	NPC481420
0.5824	Remote Similarity	NPC481421
0.5816	Remote Similarity	NPC264101
0.58	Remote Similarity	NPC70204
0.5794	Remote Similarity	NPC13193
0.5766	Remote Similarity	NPC232054
0.5758	Remote Similarity	NPC215408
0.5758	Remote Similarity	NPC485601
0.5714	Remote Similarity	NPC470866
0.5648	Remote Similarity	NPC309278
0.5619	Remote Similarity	NPC42171
0.5619	Remote Similarity	NPC6806
0.5607	Remote Similarity	NPC115165
0.5586	Remote Similarity	NPC233433
0.5567	Remote Similarity	NPC210157
0.5565	Remote Similarity	NPC224314
0.5556	Remote Similarity	NPC475550
0.5505	Remote Similarity	NPC32361
0.5488	Remote Similarity	NPC248944
0.5488	Remote Similarity	NPC7479
0.5488	Remote Similarity	NPC257296
0.5472	Remote Similarity	NPC274200
0.5464	Remote Similarity	NPC131693
0.5464	Remote Similarity	NPC475436
0.5385	Remote Similarity	NPC220836
0.5385	Remote Similarity	NPC477808
0.5354	Remote Similarity	NPC481189
0.5333	Remote Similarity	NPC98696
0.5333	Remote Similarity	NPC40440
0.531	Remote Similarity	NPC477811
0.53	Remote Similarity	NPC121453
0.5268	Remote Similarity	NPC108072
0.5258	Remote Similarity	NPC481424
0.5258	Remote Similarity	NPC481422
0.5238	Remote Similarity	NPC329807
0.5221	Remote Similarity	NPC476112
0.5221	Remote Similarity	NPC307534
0.5189	Remote Similarity	NPC202898
0.5158	Remote Similarity	NPC481418
0.5138	Remote Similarity	NPC151134
0.5128	Remote Similarity	NPC94086
0.5128	Remote Similarity	NPC473817
0.5119	Remote Similarity	NPC227260
0.5089	Remote Similarity	NPC473518
0.5088	Remote Similarity	NPC470862
0.5077	Remote Similarity	NPC329727
0.5051	Remote Similarity	NPC485602
0.505	Remote Similarity	NPC292467
0.5048	Remote Similarity	NPC475670
0.5044	Remote Similarity	NPC232611

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC244757 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7729
0.1-0.2	1340
0.2-0.3	67
0.3-0.4	6
0.4-0.5	4
0.5-0.6	2
0.6-0.7	1
0.7-0.8	1
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
0.7738	Intermediate Similarity	NPD8171	Phase 2
0.6526	Remote Similarity	NPD8170	Phase 2
0.5488	Remote Similarity	NPD6928	Phase 2
0.5376	Remote Similarity	NPD7991	Discontinued

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