NPASS Compound

Natural Product: NPC44723

Natural Product ID	NPC44723
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IZWDXDONQAMEHX-BZMKVPAPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	3035561
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 121127 0 0 0 0 0 0 0 0999 V2000 -10.0883 1.6520 -0.9918 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7573 2.1125 -0.4232 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8165 1.9998 1.0656 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6627 0.6206 1.6105 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5856 -0.1912 0.8691 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7926 -0.8688 1.9665 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5057 -1.4365 1.5005 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6626 -0.4040 0.7836 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3142 0.6668 1.7705 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4242 0.2812 -0.3154 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9696 0.4896 -1.5303 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5861 0.0639 -1.9975 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7856 -0.0187 -0.7119 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3156 -0.1105 -0.8506 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9842 0.5621 -2.1547 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6565 0.7633 0.2193 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8216 0.7564 0.2185 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4405 -0.6256 0.1807 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7368 -1.5701 -0.7199 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2258 -1.4065 -2.1791 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1748 -2.9728 -0.3644 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9534 -3.3779 0.9151 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7719 -1.4898 -0.6689 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2110 -2.0572 0.6312 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5647 -1.6790 1.1417 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4681 -1.0547 0.1205 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0169 -2.2073 -0.7012 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7791 -0.4953 -0.1622 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6278 -0.8070 0.8990 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6710 -1.8128 0.6220 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0705 -1.4517 1.0672 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4497 -0.1045 0.4992 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1687 0.7128 0.3293 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2640 0.3744 1.3638 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4161 0.5475 1.1734 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6033 0.8395 0.5933 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8509 2.3375 0.4433 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2222 2.6231 -0.0613 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2844 1.6870 0.3929 C 0 0 1 0 0 0 0 0 0 0 0 0 10.7523 0.2782 0.3037 C 0 0 1 0 0 0 0 0 0 0 0 0 11.8135 -0.7659 0.5555 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8575 -0.6446 -0.3556 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6981 0.1885 1.1887 O 0 0 0 0 0 0 0 0 0 0 0 0 12.3724 1.7834 -0.4721 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5875 3.9402 0.2945 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9530 2.7781 -0.5587 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9190 -2.4054 0.5114 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3401 -3.0382 1.2591 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4237 1.6500 -0.6675 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7853 0.7862 0.0879 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5857 1.3448 -1.0380 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2983 -1.2122 0.0917 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5741 -1.3243 0.1331 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6853 -2.1400 -0.7485 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6696 3.5750 -0.7654 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5699 4.4271 0.1309 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6993 3.9864 -2.0869 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9629 0.7587 -1.6377 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7852 1.3472 -0.1765 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6070 2.4289 -1.5807 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1366 2.7504 1.5479 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8480 2.3531 1.3611 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4287 0.7167 2.6900 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6534 0.0924 1.5788 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4359 -1.7368 2.3020 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7476 -0.1975 2.8233 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7367 -2.3204 0.8716 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9310 -1.7838 2.3675 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2657 0.7791 2.0241 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6494 1.6980 1.4498 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8485 0.5185 2.7528 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5849 0.9779 -2.2653 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6470 -0.8410 -2.5801 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2594 0.8744 -2.6762 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9978 0.9883 -0.2290 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4124 0.1044 -3.0403 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4983 1.5778 -2.0716 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0508 0.8241 -2.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0382 0.5795 1.2211 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9811 1.8133 -0.0453 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1262 1.1825 1.2267 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4263 -1.0101 1.2438 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9372 -0.5623 -2.2600 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4116 -1.4311 -2.8999 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8722 -2.2880 -2.4834 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2960 -2.9945 -0.5260 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8155 -3.7095 -1.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8588 -4.3464 0.9480 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0867 -2.1205 -1.5580 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2376 -3.1823 0.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4854 -1.7182 1.4033 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1335 -2.5951 1.5047 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5143 -1.0798 2.0928 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0122 -1.9791 -1.1250 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1549 -3.1167 -0.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3974 -2.5323 -1.5286 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0069 -1.1222 1.7892 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6587 -2.0667 -0.4781 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0772 -1.4659 2.1711 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8190 -0.3090 -0.5250 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6444 0.4736 -0.6168 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3423 1.7850 0.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5789 0.4509 -0.4478 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6935 2.8795 1.3968 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2297 2.6105 -1.1863 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6531 1.9301 1.4105 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3556 0.1387 -0.7210 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3342 -1.7554 0.3488 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1916 -0.7594 1.5798 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0248 -1.4746 -0.8565 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2090 2.0379 -0.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7759 3.9229 1.2812 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8363 3.7412 -0.5502 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7169 -2.5893 1.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2276 -2.9039 2.2310 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3211 1.3954 -0.9267 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5472 1.6575 0.7599 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0440 2.1023 -1.6486 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0258 0.5488 -1.6637 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0304 -3.1089 -0.7354 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0362 4.9055 -2.3716 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 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 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 19 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 18 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 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 40 43 1 0 39 44 1 0 38 45 1 0 37 46 1 0 31 47 1 0 30 48 1 0 17 49 1 0 10 50 1 0 50 51 1 0 5 52 1 6 52 53 2 0 52 54 1 0 2 55 1 0 55 56 2 0 55 57 1 0 51 2 1 0 50 5 1 0 26 8 1 0 34 29 1 0 43 36 1 0 26 13 1 0 23 14 1 0 1 58 1 0 1 59 1 0 1 60 1 0 3 61 1 0 3 62 1 0 4 63 1 0 4 64 1 0 6 65 1 0 6 66 1 0 7 67 1 0 7 68 1 0 9 69 1 0 9 70 1 0 9 71 1 0 11 72 1 0 12 73 1 0 12 74 1 0 13 75 1 1 15 76 1 0 15 77 1 0 15 78 1 0 16 79 1 0 16 80 1 0 17 81 1 1 18 82 1 1 20 83 1 0 20 84 1 0 20 85 1 0 21 86 1 0 21 87 1 0 22 88 1 0 23 89 1 0 24 90 1 0 24 91 1 0 25 92 1 0 25 93 1 0 27 94 1 0 27 95 1 0 27 96 1 0 29 97 1 1 30 98 1 6 31 99 1 1 32100 1 6 33101 1 0 33102 1 0 36103 1 6 37104 1 1 38105 1 6 39106 1 1 40107 1 6 41108 1 0 41109 1 0 42110 1 0 44111 1 0 45112 1 0 46113 1 0 47114 1 0 48115 1 0 49116 1 0 50117 1 1 51118 1 0 51119 1 0 54120 1 0 57121 1 0 M END

Standard InCHIKey	IZWDXDONQAMEHX-BZMKVPAPSA-N
Standard InCHI	InChI=1S/C41H64O16/c1-36(34(50)51)10-12-41(35(52)53)13-11-39(4)19(20(41)14-36)6-7-25-37(2)15-21(44)31(38(3,18-43)24(37)8-9-40(25,39)5)57-32-29(48)27(46)23(17-54-32)56-33-30(49)28(47)26(45)22(16-42)55-33/h6,20-33,42-49H,7-18H2,1-5H3,(H,50,51)(H,52,53)/t20-,21+,22-,23-,24?,25-,26-,27+,28+,29-,30-,31+,32+,33+,36-,37+,38+,39-,40-,41+/m1/s1
SMILES	C[C@]1(CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H]([C@@H]([C@@](C)(CO)C5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)O)O)[C@H]2C1)C(=O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	812.42	Volume:	790.531 ? Van der Waals volume.
Dense:	1.028	LogP:	0.462 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.452 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.976 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	40.0
TPSA:	273.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	7.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.118	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.024	Fsp³:	0.902
MCE-18:	155.077 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.714	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.168	Promiscuous compounds:	0.095

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.651	MDCK Permeability:	-5.068
Pgp-inhibitor:	0.0	Pgp-substrate:	0.12
PAMPA:	1.0 ? 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):	0.001
20% Bioavailability (F20%):	0.006	30% Bioavailability (F30%):	0.004
50% Bioavailability (F50%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.922
Plasma Protein Binding (PPB):	75.459%	Volume Distribution (VD):	-0.416
Fu:	16.831% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.319	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
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):

0.236

Half-life (T1/2):

2.793

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.816	Drug-induced Liver Injury (DILI):	0.908
AMES Toxicity:	0.755	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.005	Skin Sensitization:	1.0
Carcinogencity:	0.28	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.022
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.996
Hematotoxicity:	0.714	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.478	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.212	Hek293 Cytotoxicity:	0.019
BCF:	0.436 ? 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:	3.322 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.008 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.891 ? 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
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932140]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	roots	n.a.	n.a.	PMID[18177012]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[26595875]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	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 NPC44723 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	21378
0.1-0.2	23222
0.2-0.3	3785
0.3-0.4	1012
0.4-0.5	379
0.5-0.6	66
0.6-0.7	10
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
0.8298	Intermediate Similarity	NPC473383
0.7553	Intermediate Similarity	NPC136877
0.6796	Remote Similarity	NPC473405
0.6465	Remote Similarity	NPC127853
0.6408	Remote Similarity	NPC473343
0.6383	Remote Similarity	NPC204407
0.6321	Remote Similarity	NPC139044
0.6275	Remote Similarity	NPC59804
0.6214	Remote Similarity	NPC480424
0.6162	Remote Similarity	NPC284807
0.6087	Remote Similarity	NPC219180
0.6	Remote Similarity	NPC475633
0.598	Remote Similarity	NPC270667
0.5979	Remote Similarity	NPC606107
0.5963	Remote Similarity	NPC257468
0.5909	Remote Similarity	NPC119794
0.5905	Remote Similarity	NPC127056
0.5893	Remote Similarity	NPC488564
0.5872	Remote Similarity	NPC471383
0.5865	Remote Similarity	NPC12288
0.5862	Remote Similarity	NPC323341
0.5825	Remote Similarity	NPC164194
0.5816	Remote Similarity	NPC57362
0.5804	Remote Similarity	NPC323359
0.5714	Remote Similarity	NPC276093
0.5701	Remote Similarity	NPC472949
0.566	Remote Similarity	NPC174679
0.566	Remote Similarity	NPC279554
0.5657	Remote Similarity	NPC28198
0.5657	Remote Similarity	NPC476123
0.5636	Remote Similarity	NPC104400
0.5636	Remote Similarity	NPC10320
0.5614	Remote Similarity	NPC488209
0.561	Remote Similarity	NPC471385
0.5556	Remote Similarity	NPC488561
0.5556	Remote Similarity	NPC488516
0.5546	Remote Similarity	NPC166422
0.5545	Remote Similarity	NPC31839
0.5514	Remote Similarity	NPC25605
0.5505	Remote Similarity	NPC80843
0.55	Remote Similarity	NPC475140
0.547	Remote Similarity	NPC288205
0.547	Remote Similarity	NPC51465
0.547	Remote Similarity	NPC476992
0.5463	Remote Similarity	NPC473373
0.5462	Remote Similarity	NPC133818
0.5455	Remote Similarity	NPC54636
0.5429	Remote Similarity	NPC51947
0.5405	Remote Similarity	NPC114304
0.5391	Remote Similarity	NPC324875
0.5391	Remote Similarity	NPC292677
0.5391	Remote Similarity	NPC291903
0.537	Remote Similarity	NPC139894
0.5364	Remote Similarity	NPC471547
0.536	Remote Similarity	NPC161717
0.5357	Remote Similarity	NPC180550
0.5357	Remote Similarity	NPC35405
0.5351	Remote Similarity	NPC79718
0.5351	Remote Similarity	NPC488515
0.5327	Remote Similarity	NPC179434
0.5321	Remote Similarity	NPC150400
0.5321	Remote Similarity	NPC109079
0.5268	Remote Similarity	NPC471548
0.5254	Remote Similarity	NPC62725
0.525	Remote Similarity	NPC151543
0.5229	Remote Similarity	NPC56713
0.5225	Remote Similarity	NPC22956
0.5221	Remote Similarity	NPC473401
0.521	Remote Similarity	NPC475119
0.5207	Remote Similarity	NPC471384
0.5196	Remote Similarity	NPC283849
0.5185	Remote Similarity	NPC475208
0.5167	Remote Similarity	NPC473824
0.5164	Remote Similarity	NPC251263
0.5146	Remote Similarity	NPC177246
0.5133	Remote Similarity	NPC109588
0.5048	Remote Similarity	NPC100383
0.5042	Remote Similarity	NPC475486

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC44723 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6616
0.1-0.2	2462
0.2-0.3	65
0.3-0.4	7
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