NPASS Compound

Natural Product: NPC471965

Natural Product ID	NPC471965
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DTMJARJUCFBMFR-ZHGMGIEYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3314504
PubChem CID	n.a.
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 117123 0 0 0 0 0 0 0 0999 V2000 -1.6272 0.7716 2.8261 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2896 0.6063 1.7853 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7309 0.3866 1.8942 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5102 0.3710 0.8163 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9498 0.1415 1.0445 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2248 -1.0273 1.9220 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8710 -2.2101 1.2909 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3005 -3.5239 1.8715 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6787 -2.3119 -0.1836 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1437 -1.0660 -0.8418 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8072 0.2177 -0.1515 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1666 0.7891 0.3260 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3415 1.1990 -1.1895 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9077 1.2584 -1.4940 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9911 0.5756 -0.5513 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6926 1.4152 -0.4246 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7651 0.6070 0.4025 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3136 0.9343 0.2901 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1557 2.0825 1.0976 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4399 -0.2945 0.8315 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9301 -0.0964 0.6763 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2568 -0.0236 -0.7686 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4384 0.9736 -1.5484 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0049 0.9970 -1.1740 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7131 2.1553 -1.7695 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1985 1.7995 -1.7697 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0967 2.3365 -1.6136 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4743 0.4430 -2.9998 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6192 0.2311 -0.9138 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3135 -0.7853 -1.5185 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8381 -0.4011 -2.7675 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9165 0.4528 -2.4888 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1804 1.3494 -3.6438 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1198 2.1759 -3.5475 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4139 1.2762 -4.7921 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1061 -0.4497 -2.2211 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5830 -1.7299 -1.5924 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3814 -1.4137 -0.6911 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8372 -0.6575 0.3585 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7656 -1.3527 1.5687 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9421 -0.7547 2.4890 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4353 0.4174 3.0145 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6611 0.0549 3.8474 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7092 -0.4310 2.8761 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1475 -1.6141 2.1359 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0245 -2.6598 3.0461 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1459 0.5650 2.0191 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1144 1.1302 4.5990 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1734 -2.5484 -2.6438 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9996 0.2060 -1.4095 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1514 2.6924 0.2805 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6017 -0.7727 -1.1379 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3162 -2.2468 1.6222 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2530 -2.2296 0.8013 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6895 -2.3066 2.9785 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1494 0.2342 2.9027 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2497 1.0499 1.6840 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8476 -0.7689 2.8337 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2707 -1.4080 2.4031 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2735 -3.7024 1.4950 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9894 -4.3562 1.7365 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2124 -3.3412 2.9775 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3627 -3.1539 -0.5227 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6614 -2.6543 -0.4711 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2616 -1.1756 -1.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7643 -1.0701 -1.9138 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2920 0.6409 1.4116 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2277 1.8769 0.1500 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0082 0.3230 -0.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6901 2.2451 -0.9216 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9165 1.0169 -2.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7353 0.7861 -2.5148 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6272 2.3258 -1.6889 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8515 -0.4722 0.0738 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1471 2.4063 0.7160 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3731 1.7640 2.1597 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4893 2.9761 1.0692 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1361 -0.5311 1.8564 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1586 -1.1352 0.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3125 0.7560 1.2723 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4088 -1.0063 1.0956 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0781 -1.0510 -1.2042 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4587 0.0643 -1.6175 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4435 2.3621 -2.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6418 3.0864 -1.1426 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6979 2.7501 -2.1253 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3459 1.0745 -2.5677 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9397 2.4249 -0.8660 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3783 3.1712 -1.5393 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6278 2.5129 -2.5961 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5943 0.7685 -3.5641 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4731 -0.6654 -2.9847 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3725 0.8519 -3.5073 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5659 -1.5986 -1.7536 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7159 1.0239 -1.5746 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5348 2.0078 -5.5094 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6078 -0.7241 -3.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3419 -2.2708 -1.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0666 -2.4120 -0.2853 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3396 -2.3804 1.3693 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6851 0.8147 3.7223 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7554 1.1425 2.2466 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4004 -0.8112 4.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5854 -0.8262 3.4693 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8492 -1.8549 1.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8888 -3.0112 3.3609 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6569 0.1000 1.2851 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1348 0.8433 5.5670 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4328 -2.2040 -3.5217 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9347 -0.0391 -1.6457 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6760 3.5950 -0.1829 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8561 2.6954 1.3454 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2314 2.8449 0.2417 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6916 -0.7541 -1.7420 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5085 -1.5655 -0.3703 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3973 -1.1553 -1.8441 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6561 -2.1407 3.2609 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 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 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 23 27 1 0 23 28 1 0 22 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 32 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 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 37 49 1 0 36 50 1 0 16 51 1 1 15 52 1 6 7 53 1 0 53 54 2 0 53 55 1 0 17 2 1 0 24 18 1 0 38 30 1 0 45 40 1 0 15 4 1 0 26 16 1 0 11 5 1 0 3 56 1 0 5 57 1 1 6 58 1 0 6 59 1 0 8 60 1 0 8 61 1 0 8 62 1 0 9 63 1 0 9 64 1 0 10 65 1 0 10 66 1 0 12 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 17 74 1 6 19 75 1 0 19 76 1 0 19 77 1 0 20 78 1 0 20 79 1 0 21 80 1 0 21 81 1 0 22 82 1 6 24 83 1 6 25 84 1 0 25 85 1 0 26 86 1 0 26 87 1 0 27 88 1 0 27 89 1 0 27 90 1 0 28 91 1 0 28 92 1 0 28 93 1 0 30 94 1 6 32 95 1 1 35 96 1 0 36 97 1 6 37 98 1 1 38 99 1 1 40100 1 6 42101 1 0 42102 1 0 43103 1 1 44104 1 1 45105 1 6 46106 1 0 47107 1 0 48108 1 0 49109 1 0 50110 1 0 51111 1 0 51112 1 0 51113 1 0 52114 1 0 52115 1 0 52116 1 0 55117 1 0 M END

Standard InCHIKey	DTMJARJUCFBMFR-ZHGMGIEYSA-N
Standard InCHI	InChI=1S/C41H62O14/c1-36(2)23-8-11-41(7)31(21(42)16-19-20-17-38(4,35(50)51)13-12-37(20,3)14-15-40(19,41)6)39(23,5)10-9-24(36)53-34-30(27(46)26(45)29(54-34)32(48)49)55-33-28(47)25(44)22(43)18-52-33/h16,20,22-31,33-34,43-47H,8-15,17-18H2,1-7H3,(H,48,49)(H,50,51)/t20-,22-,23-,24-,25-,26-,27-,28+,29-,30+,31+,33-,34-,37+,38-,39-,40+,41+/m0/s1
SMILES	O=C1C=C2[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@]2([C@]2([C@H]1[C@@]1(C)CC[C@@H](C([C@@H]1CC2)(C)C)O[C@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O)O)C)C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	778.41	Volume:	770.314 ? Van der Waals volume.
Dense:	1.011	LogP:	1.902 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.133 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.399 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	41.0
TPSA:	229.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.193	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.839	Fsp³:	0.878
MCE-18:	154.182 ? 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:	0.85	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.107 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.131	Promiscuous compounds:	0.265

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.084	MDCK Permeability:	-5.169
Pgp-inhibitor:	0.0	Pgp-substrate:	0.615
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):	0.0
20% Bioavailability (F20%):	0.124	30% Bioavailability (F30%):	0.002
50% Bioavailability (F50%):	0.854

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.984
Plasma Protein Binding (PPB):	73.303%	Volume Distribution (VD):	-0.559
Fu:	22.481% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.11
OATP1B3 inhibitor:	0.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.001

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:	1.0	CYP3A4-substrate:	0.934
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.002
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):

0.486

Half-life (T1/2):

2.535

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.646	Drug-induced Liver Injury (DILI):	0.827
AMES Toxicity:	0.199	Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.033	Skin Sensitization:	1.0
Carcinogencity:	0.113	Eye Corrosion:	0.0
Eye Irritation:	0.132	Respiratory Toxicity:	0.169
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.956
Hematotoxicity:	0.375	Drug-induced Nephrotoxicity:	0.996
Genotoxicity:	0.886	RPMI-8226 Immunitoxicity:	0.084
A549 Cytotoxicity:	0.03	Hek293 Cytotoxicity:	0.039
BCF:	0.551 ? 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:	3.622 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.436 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.484 ? 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
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11164-015-2099-x]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1134/S1021443711030101]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	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
IC50	1
Inhibition	1

Activity Type	# Activity
Organism	2

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
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	85100.0	nM	PMID[17850214]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	>	50.0	%	PMID[25763602]

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 NPC471965 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	19725
0.1-0.2	25901
0.2-0.3	3330
0.3-0.4	667
0.4-0.5	179
0.5-0.6	14
0.6-0.7	18
0.7-0.8	0
0.8-0.85	4
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC482749
0.8901	High Similarity	NPC482747
0.8901	High Similarity	NPC202666
0.8901	High Similarity	NPC471961
0.8901	High Similarity	NPC242015
0.8542	High Similarity	NPC262199
0.8021	Intermediate Similarity	NPC482741
0.8021	Intermediate Similarity	NPC482745
0.8021	Intermediate Similarity	NPC482743
0.8021	Intermediate Similarity	NPC146753
0.7857	Intermediate Similarity	NPC14617
0.7826	Intermediate Similarity	NPC482752
0.7353	Intermediate Similarity	NPC482734
0.7353	Intermediate Similarity	NPC182342
0.7353	Intermediate Similarity	NPC482727
0.7353	Intermediate Similarity	NPC471964
0.7245	Intermediate Similarity	NPC482750
0.72	Intermediate Similarity	NPC482746
0.7156	Intermediate Similarity	NPC482739
0.7143	Intermediate Similarity	NPC482737
0.7143	Intermediate Similarity	NPC482735
0.7071	Intermediate Similarity	NPC309780
0.7053	Intermediate Similarity	NPC471967
0.6881	Remote Similarity	NPC471962
0.6762	Remote Similarity	NPC482729
0.6762	Remote Similarity	NPC482742
0.6731	Remote Similarity	NPC285091
0.6729	Remote Similarity	NPC247315
0.6729	Remote Similarity	NPC482728
0.6699	Remote Similarity	NPC482717
0.6637	Remote Similarity	NPC482736
0.6637	Remote Similarity	NPC482738
0.6636	Remote Similarity	NPC482755
0.6604	Remote Similarity	NPC482744
0.6574	Remote Similarity	NPC482740
0.6449	Remote Similarity	NPC482722
0.6449	Remote Similarity	NPC471963
0.6373	Remote Similarity	NPC482726
0.6346	Remote Similarity	NPC482748
0.6264	Remote Similarity	NPC74751
0.6087	Remote Similarity	NPC482712
0.587	Remote Similarity	NPC4036
0.587	Remote Similarity	NPC65120
0.587	Remote Similarity	NPC145067
0.587	Remote Similarity	NPC233455
0.587	Remote Similarity	NPC158030
0.5833	Remote Similarity	NPC482751
0.5789	Remote Similarity	NPC301449
0.5789	Remote Similarity	NPC601290
0.5455	Remote Similarity	NPC275343
0.5268	Remote Similarity	NPC472949
0.5217	Remote Similarity	NPC251768
0.5213	Remote Similarity	NPC96095
0.5175	Remote Similarity	NPC469945
0.5133	Remote Similarity	NPC488561

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471965 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6085
0.1-0.2	3010
0.2-0.3	47
0.3-0.4	1
0.4-0.5	3
0.5-0.6	2
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8901	High Similarity	NPD8328	Phase 2
0.6264	Remote Similarity	NPD7748	Pre-clinical
0.5938	Remote Similarity	NPD7902	Phase 4
0.587	Remote Similarity	NPD7515	Phase 2

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