NPASS Compound

Natural Product: NPC90856

Natural Product ID	NPC90856
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oblonganoside L
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-10-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2253400
PubChem CID	76311973
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene 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 120126 0 0 0 0 0 0 0 0999 V2000 6.6513 4.4769 2.0035 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9624 4.5093 0.6460 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1781 3.1019 0.1633 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0209 2.3673 0.3654 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9584 1.2444 -0.4564 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8318 0.4936 -0.0389 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9465 -0.8098 0.4315 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1025 -1.2945 0.4669 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7646 -1.6065 0.8763 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1662 -0.8288 2.0196 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1323 0.1907 1.5251 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9633 -0.6461 0.9731 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5500 -1.2460 -0.2547 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9307 -1.2472 -1.4288 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4214 -0.6463 -1.6428 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0679 -0.4971 -0.3147 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2258 0.2459 0.6407 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2673 1.5745 0.0412 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8642 0.6372 1.9367 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3381 0.9901 1.8042 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0059 -0.1133 1.0332 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5338 -0.0808 -0.3728 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7454 1.1678 -1.1321 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2922 -1.1872 -1.1010 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7634 -1.0740 -1.0394 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3098 -0.1332 0.0337 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4818 -0.2285 1.2560 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8279 -1.6197 1.8534 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9020 0.7360 2.3358 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6175 1.0942 -0.4790 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9421 1.3935 -0.6106 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3048 1.4221 -1.9964 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5955 1.8497 -2.1726 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4267 1.9534 -0.9392 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7963 2.7401 0.1666 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2774 2.7449 -0.0916 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5950 3.0590 1.0664 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2297 4.0592 0.2147 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9294 0.7198 -0.4984 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9079 -1.9077 -0.2626 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6735 -3.3143 -0.6517 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5163 -4.3909 -0.1241 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7789 -3.8508 0.4900 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3798 -2.8525 1.5339 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9854 -5.2817 -1.2871 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7913 -5.3215 0.8347 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6685 -6.3051 1.2829 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5898 -1.7303 1.9410 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7503 1.6101 -1.9086 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5132 2.8627 -2.2441 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6360 3.0709 -1.2719 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6490 2.1397 -1.4628 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6759 3.9711 -2.2799 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3062 0.5679 -2.6605 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8649 3.5970 2.3660 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0688 4.9307 0.1356 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8401 5.1586 0.4468 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9764 2.6494 0.7966 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8493 0.5902 -0.3212 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9447 -0.1871 2.5308 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7705 -1.4751 2.8220 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8387 0.8389 2.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6436 0.6845 0.6737 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3776 -1.6934 -2.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0030 -1.4380 -2.2030 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3802 0.2117 -2.2982 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1448 -1.5646 0.0693 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1113 1.9915 0.6510 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5493 2.3307 0.2473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5480 1.4914 -0.9998 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3955 1.5489 2.3694 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7623 -0.1303 2.7324 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7352 0.9510 2.8445 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5147 1.9980 1.4402 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5707 -1.0512 1.4874 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3971 1.0526 -2.0504 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7678 1.4784 -1.6063 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0663 2.0447 -0.5774 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8928 -2.1813 -0.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0015 -1.0665 -2.1866 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1708 -2.1138 -0.8877 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2411 -0.7436 -2.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3222 -0.5939 0.2716 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8776 -1.8639 1.6999 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5239 -1.6733 2.9030 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2206 -2.3524 1.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0143 0.7105 2.3618 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4880 1.7481 2.2109 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5996 0.2826 3.3269 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6252 0.6356 -0.1682 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1023 1.0893 -2.8376 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6693 2.8051 -2.7346 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3519 2.5316 -1.2361 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9475 2.2975 1.1721 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0814 3.4946 -0.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3648 4.0123 1.1537 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0209 4.5019 -0.6694 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2444 0.8369 0.4371 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3944 -1.4195 -1.1746 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6477 -3.3925 -1.7812 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5966 -3.5935 -0.3881 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3739 -3.3645 -0.2926 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3605 -4.6390 1.0180 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7380 -3.2894 2.2946 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2981 -2.5031 2.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3811 -4.6068 -2.0740 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1618 -5.9294 -1.6250 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8491 -5.8552 -0.8908 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4574 -4.7350 1.7011 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9601 -5.8049 0.2839 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8109 -7.0159 0.6013 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2125 -2.6545 1.7611 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4541 -2.0831 1.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7508 -1.4328 3.0060 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6786 1.6664 -2.1071 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9804 2.7935 -3.2596 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0743 4.0741 -1.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3925 2.2949 -0.8409 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9064 3.8661 -1.6727 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8876 0.4780 -3.5504 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 7 8 2 0 9 7 1 6 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 26 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 35 38 1 0 34 39 1 0 13 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 6 42 46 1 0 46 47 1 0 12 48 1 1 5 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 51 3 1 0 44 9 1 0 40 9 1 0 17 12 1 0 27 21 1 0 36 31 1 0 22 16 1 0 1 55 1 0 2 56 1 0 2 57 1 0 3 58 1 1 5 59 1 6 10 60 1 0 10 61 1 0 11 62 1 0 11 63 1 0 14 64 1 0 15 65 1 0 15 66 1 0 16 67 1 1 18 68 1 0 18 69 1 0 18 70 1 0 19 71 1 0 19 72 1 0 20 73 1 0 20 74 1 0 21 75 1 1 23 76 1 0 23 77 1 0 23 78 1 0 24 79 1 0 24 80 1 0 25 81 1 0 25 82 1 0 26 83 1 1 28 84 1 0 28 85 1 0 28 86 1 0 29 87 1 0 29 88 1 0 29 89 1 0 31 90 1 1 33 91 1 0 33 92 1 0 34 93 1 6 35 94 1 1 36 95 1 6 37 96 1 0 38 97 1 0 39 98 1 0 40 99 1 6 41100 1 0 41101 1 0 43102 1 0 43103 1 0 44104 1 0 44105 1 0 45106 1 0 45107 1 0 45108 1 0 46109 1 0 46110 1 0 47111 1 0 48112 1 0 48113 1 0 48114 1 0 49115 1 1 50116 1 6 51117 1 6 52118 1 0 53119 1 0 54120 1 0 M END

Standard InCHIKey	JUQZBNSNCFPQEN-OKBJWFIMSA-N
Standard InCHI	InChI=1S/C41H66O13/c1-36(2)25-9-12-40(6)26(38(25,4)11-10-27(36)53-33-31(48)28(45)23(44)19-51-33)8-7-21-22-17-37(3,20-43)13-15-41(22,16-14-39(21,40)5)35(50)54-34-32(49)30(47)29(46)24(18-42)52-34/h7,22-34,42-49H,8-20H2,1-6H3/t22-,23+,24+,25-,26+,27-,28-,29+,30-,31+,32+,33-,34-,37+,38-,39+,40+,41-/m0/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)[C@]23CC[C@@]4(C(=CC[C@H]5[C@@]4(C)CC[C@@H]4[C@]5(C)CC[C@@H](C4(C)C)O[C@@H]4OC[C@H]([C@@H]([C@H]4O)O)O)[C@@H]3C[C@](CC2)(C)CO)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	766.45	Volume:	766.797 ? Van der Waals volume.
Dense:	1.0	LogP:	1.94 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.324 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.206 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	39.0
TPSA:	215.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.11	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.829	Fsp³:	0.927
MCE-18:	149.013 ? 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:	0.952	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.172	Promiscuous compounds:	0.054

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.234	MDCK Permeability:	-5.027
Pgp-inhibitor:	0.0	Pgp-substrate:	0.013
PAMPA:	0.999 ? 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):	0.009
20% Bioavailability (F20%):	0.781	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.92	MRP1:	0.01
Plasma Protein Binding (PPB):	69.292%	Volume Distribution (VD):	-0.332
Fu:	22.388% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.181
BSEP inhibitor:	0.007

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.006	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.011 ? 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):

0.658

Half-life (T1/2):

2.989

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.057
Human Hepatotoxicity (H-HT):	0.706	Drug-induced Liver Injury (DILI):	0.576
AMES Toxicity:	0.824	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.034	Skin Sensitization:	1.0
Carcinogencity:	0.248	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.99
Hematotoxicity:	0.371	Drug-induced Nephrotoxicity:	0.942
Genotoxicity:	0.228	RPMI-8226 Immunitoxicity:	0.106
A549 Cytotoxicity:	0.53	Hek293 Cytotoxicity:	0.388
BCF:	1.77 ? 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:	4.037 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.651 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.844 ? 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
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27642865]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235013]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39409699]
NPO9182	Lychnophora passerina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26048	Grateloupia elliptica	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24698	Protium unifoliolatum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4318	Aspergillus cristatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26283	Streptomyces djakartensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25339	Trillium smallii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25649	Calliandra haematocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26345	Sideroxylon tomentosum	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25992	Lasallia papulosa	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24698	Protium unifoliolatum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25765	Dryopteris aemula	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26399	Crepidiastrum lanceolatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4318	Aspergillus cristatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26048	Grateloupia elliptica	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26283	Streptomyces djakartensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28950	Angelonia integerrima	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9182	Lychnophora passerina	Species	Asteraceae	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
Inhibition	1

Activity Type	# Activity
Organism	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
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	46.9	%	PMID[17274628]

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 NPC90856 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	19898
0.1-0.2	24626
0.2-0.3	3747
0.3-0.4	968
0.4-0.5	385
0.5-0.6	116
0.6-0.7	58
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	NPC128925
0.7912	Intermediate Similarity	NPC469946
0.7727	Intermediate Similarity	NPC204458
0.764	Intermediate Similarity	NPC78046
0.7609	Intermediate Similarity	NPC295371
0.7556	Intermediate Similarity	NPC48499
0.75	Intermediate Similarity	NPC297263
0.7391	Intermediate Similarity	NPC475516
0.7386	Intermediate Similarity	NPC256798
0.7374	Intermediate Similarity	NPC480474
0.7333	Intermediate Similarity	NPC214484
0.7273	Intermediate Similarity	NPC301449
0.7273	Intermediate Similarity	NPC601290
0.7143	Intermediate Similarity	NPC189884
0.7143	Intermediate Similarity	NPC138334
0.7129	Intermediate Similarity	NPC31838
0.7129	Intermediate Similarity	NPC481078
0.7129	Intermediate Similarity	NPC187290
0.71	Intermediate Similarity	NPC481079
0.7083	Intermediate Similarity	NPC112352
0.7053	Intermediate Similarity	NPC39211
0.7045	Intermediate Similarity	NPC68419
0.7041	Intermediate Similarity	NPC63159
0.7021	Intermediate Similarity	NPC235405
0.7021	Intermediate Similarity	NPC139894
0.6947	Remote Similarity	NPC249848
0.6947	Remote Similarity	NPC107966
0.6939	Remote Similarity	NPC480475
0.6882	Remote Similarity	NPC1046
0.6875	Remote Similarity	NPC157868
0.6863	Remote Similarity	NPC295823
0.6863	Remote Similarity	NPC174720
0.6863	Remote Similarity	NPC475467
0.6771	Remote Similarity	NPC473373
0.6735	Remote Similarity	NPC223301
0.6735	Remote Similarity	NPC171544
0.6729	Remote Similarity	NPC123199
0.67	Remote Similarity	NPC235438
0.6697	Remote Similarity	NPC481080
0.6667	Remote Similarity	NPC30735
0.6667	Remote Similarity	NPC161434
0.6629	Remote Similarity	NPC237503
0.66	Remote Similarity	NPC40775
0.66	Remote Similarity	NPC251768
0.66	Remote Similarity	NPC159309
0.66	Remote Similarity	NPC46665
0.66	Remote Similarity	NPC86222
0.6591	Remote Similarity	NPC167383
0.6566	Remote Similarity	NPC192791
0.6538	Remote Similarity	NPC480473
0.6535	Remote Similarity	NPC475591
0.6535	Remote Similarity	NPC236870
0.6505	Remote Similarity	NPC104372
0.6471	Remote Similarity	NPC222580
0.6465	Remote Similarity	NPC263756
0.6465	Remote Similarity	NPC213674
0.6458	Remote Similarity	NPC179434
0.6436	Remote Similarity	NPC10607
0.6429	Remote Similarity	NPC58448
0.6389	Remote Similarity	NPC79643
0.6381	Remote Similarity	NPC241909
0.6364	Remote Similarity	NPC473884
0.6354	Remote Similarity	NPC29069
0.6346	Remote Similarity	NPC281148
0.6346	Remote Similarity	NPC114484
0.6306	Remote Similarity	NPC488560
0.6273	Remote Similarity	NPC135904
0.6261	Remote Similarity	NPC481081
0.6226	Remote Similarity	NPC80986
0.6216	Remote Similarity	NPC475160
0.6216	Remote Similarity	NPC473714
0.6195	Remote Similarity	NPC57484
0.6176	Remote Similarity	NPC160415
0.6176	Remote Similarity	NPC309714
0.6146	Remote Similarity	NPC195132
0.6111	Remote Similarity	NPC11242
0.6078	Remote Similarity	NPC75417
0.6078	Remote Similarity	NPC242840
0.6058	Remote Similarity	NPC148417
0.605	Remote Similarity	NPC250247
0.6042	Remote Similarity	NPC209894
0.6	Remote Similarity	NPC60557
0.6	Remote Similarity	NPC67857
0.598	Remote Similarity	NPC473343
0.598	Remote Similarity	NPC161674
0.5962	Remote Similarity	NPC11551
0.5948	Remote Similarity	NPC41061
0.5948	Remote Similarity	NPC227551
0.5929	Remote Similarity	NPC470218
0.5929	Remote Similarity	NPC471550
0.5913	Remote Similarity	NPC476068
0.5882	Remote Similarity	NPC70809
0.5872	Remote Similarity	NPC104137
0.5872	Remote Similarity	NPC26626
0.5847	Remote Similarity	NPC236638
0.5847	Remote Similarity	NPC294453
0.5847	Remote Similarity	NPC305981
0.5825	Remote Similarity	NPC475171
0.5824	Remote Similarity	NPC191763
0.5816	Remote Similarity	NPC47063
0.581	Remote Similarity	NPC164389
0.5798	Remote Similarity	NPC261506
0.5798	Remote Similarity	NPC4328
0.5784	Remote Similarity	NPC150400
0.5758	Remote Similarity	NPC473481
0.5758	Remote Similarity	NPC269095
0.5755	Remote Similarity	NPC68175
0.5729	Remote Similarity	NPC110139
0.5729	Remote Similarity	NPC108709
0.5714	Remote Similarity	NPC475287
0.5714	Remote Similarity	NPC109588
0.5714	Remote Similarity	NPC117714
0.5714	Remote Similarity	NPC30289
0.5701	Remote Similarity	NPC31193
0.5701	Remote Similarity	NPC475504
0.569	Remote Similarity	NPC4749
0.5684	Remote Similarity	NPC283849
0.5684	Remote Similarity	NPC37739
0.5684	Remote Similarity	NPC306746
0.5684	Remote Similarity	NPC199457
0.5678	Remote Similarity	NPC258617
0.566	Remote Similarity	NPC473459
0.5652	Remote Similarity	NPC283417
0.5652	Remote Similarity	NPC200049
0.5638	Remote Similarity	NPC46388
0.563	Remote Similarity	NPC43550
0.5625	Remote Similarity	NPC137917
0.5614	Remote Similarity	NPC475899
0.5614	Remote Similarity	NPC165204
0.5586	Remote Similarity	NPC207738
0.5583	Remote Similarity	NPC136768
0.5579	Remote Similarity	NPC116794
0.5577	Remote Similarity	NPC470512
0.5577	Remote Similarity	NPC488561
0.5575	Remote Similarity	NPC76972
0.5575	Remote Similarity	NPC469782
0.5575	Remote Similarity	NPC204414
0.5575	Remote Similarity	NPC610204
0.5534	Remote Similarity	NPC108748
0.5526	Remote Similarity	NPC123522
0.5521	Remote Similarity	NPC606107
0.5517	Remote Similarity	NPC100639
0.5517	Remote Similarity	NPC191827
0.5505	Remote Similarity	NPC79718
0.5505	Remote Similarity	NPC64715
0.5487	Remote Similarity	NPC185466
0.5481	Remote Similarity	NPC173583
0.5474	Remote Similarity	NPC605954
0.5464	Remote Similarity	NPC604133
0.5463	Remote Similarity	NPC470515
0.5462	Remote Similarity	NPC110633
0.5455	Remote Similarity	NPC202828
0.5455	Remote Similarity	NPC119592
0.5424	Remote Similarity	NPC85154
0.5413	Remote Similarity	NPC123796
0.541	Remote Similarity	NPC298034
0.541	Remote Similarity	NPC71065
0.5408	Remote Similarity	NPC271138
0.5408	Remote Similarity	NPC102914
0.5391	Remote Similarity	NPC192600
0.5377	Remote Similarity	NPC76497
0.5372	Remote Similarity	NPC293330
0.537	Remote Similarity	NPC488526
0.537	Remote Similarity	NPC102439
0.537	Remote Similarity	NPC173859
0.537	Remote Similarity	NPC232237
0.537	Remote Similarity	NPC148603
0.5357	Remote Similarity	NPC481030
0.5354	Remote Similarity	NPC220984
0.5354	Remote Similarity	NPC242611
0.5333	Remote Similarity	NPC127056
0.5333	Remote Similarity	NPC286457
0.5323	Remote Similarity	NPC224381
0.5321	Remote Similarity	NPC105800
0.5306	Remote Similarity	NPC7870
0.5306	Remote Similarity	NPC310014
0.5306	Remote Similarity	NPC269315
0.5306	Remote Similarity	NPC75747
0.5285	Remote Similarity	NPC302543
0.5278	Remote Similarity	NPC104071
0.5268	Remote Similarity	NPC606145
0.5263	Remote Similarity	NPC473844
0.5254	Remote Similarity	NPC602995
0.525	Remote Similarity	NPC21691
0.5246	Remote Similarity	NPC65105
0.5204	Remote Similarity	NPC28198
0.5204	Remote Similarity	NPC476123
0.5185	Remote Similarity	NPC45606
0.5185	Remote Similarity	NPC256133
0.5182	Remote Similarity	NPC258885
0.5175	Remote Similarity	NPC36831
0.5175	Remote Similarity	NPC609281
0.5172	Remote Similarity	NPC610461
0.5169	Remote Similarity	NPC155410
0.5169	Remote Similarity	NPC603137
0.5164	Remote Similarity	NPC470876
0.5156	Remote Similarity	NPC480422
0.5152	Remote Similarity	NPC177246
0.5135	Remote Similarity	NPC470513

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC90856 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7045
0.1-0.2	2038
0.2-0.3	58
0.3-0.4	8
0.4-0.5	1
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