NPASS Compound

Natural Product: NPC89001

Natural Product ID	NPC89001
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Uvaribonin
IUPAC Name	[(1R,3R)-3,13-dihydroxy-1-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-15-(2-methyl-5-oxo-2H-furan-4-yl)pentadecyl] acetate
Synonyms	Uvaribonin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL274745
PubChem CID	24761041
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 117118 0 0 0 0 0 0 0 0999 V2000 -14.6729 -0.4221 -1.2592 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5910 -0.9481 -2.1811 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5795 -1.7769 -1.4219 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9251 -0.9369 -0.3466 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2089 0.2391 -0.9428 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5353 1.1046 0.0667 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5068 0.4535 0.9142 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3500 -0.1536 0.2051 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5231 0.7727 -0.6191 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8875 1.8973 0.0721 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0093 1.7546 1.2198 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7403 1.0332 1.2532 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6448 -0.4287 1.0705 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1579 -0.7918 1.2255 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9534 -2.2905 1.1522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4122 -2.3027 1.0054 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2043 -1.0598 0.2163 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3960 -0.3438 0.1712 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2038 -0.0838 0.9470 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2017 1.0303 0.1188 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9147 2.2003 0.4767 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5563 2.2298 1.5586 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8962 3.3774 -0.4279 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0551 -0.7857 1.2002 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1178 -0.0275 1.9030 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5932 1.1657 1.1567 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6601 1.9204 1.8679 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8557 1.1932 2.2471 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7389 0.6095 1.2388 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2691 -0.4689 0.3292 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5792 -0.8323 -0.4971 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2519 -1.9248 -1.4379 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3734 -2.4296 -2.2298 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1164 -1.6186 -3.1894 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8612 -0.4158 -2.7851 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9461 -0.6636 -1.7293 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5599 0.6998 -1.4784 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6388 0.6661 -0.4521 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1379 -0.3091 0.2534 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1986 0.1697 1.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2953 1.5438 0.8830 O 0 0 0 0 0 0 0 0 0 0 0 0 12.3608 1.8722 -0.0702 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1743 3.0464 -0.5300 O 0 0 0 0 0 0 0 0 0 0 0 0 14.5109 -0.4698 0.7235 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6435 0.0279 -3.9323 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6176 0.3151 3.1731 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1484 -0.9611 -0.0671 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.2618 0.4503 -0.7084 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.5840 -0.1300 -1.8119 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9682 -1.1791 -0.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.1195 -1.5809 -2.9311 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1127 -0.1422 -2.7458 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8274 -2.1113 -2.1959 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0729 -2.6657 -0.9924 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6869 -0.6700 0.3831 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1336 -1.6017 0.1068 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5446 -0.0474 -1.7804 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0117 0.8883 -1.4085 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0633 1.9617 -0.4898 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3046 1.5435 0.7588 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0151 -0.3884 1.4713 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2220 1.1734 1.7065 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7430 -0.9391 -0.5069 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6899 -0.7423 0.8910 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8637 0.2498 -1.3053 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2740 1.2872 -1.3580 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2518 2.4248 -0.7451 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6547 2.7562 0.2453 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7597 2.8113 1.6590 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6376 1.3639 2.1122 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0969 1.4911 0.3987 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0966 1.3644 2.1450 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1145 -0.9316 1.9784 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8250 -0.4371 2.1977 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2590 -2.7942 2.0674 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3397 -2.7423 0.2277 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0488 -2.1523 2.0498 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0545 -3.2237 0.5452 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8301 -1.2304 -0.8033 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7307 0.1708 1.8983 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7080 3.3306 -1.1777 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0697 3.4541 -0.9723 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9634 4.2943 0.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8719 -1.7833 1.7218 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4560 -1.1220 0.1743 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9559 -0.7443 2.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8380 0.9565 0.1362 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6961 1.8909 1.0745 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2266 2.5275 2.7279 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9446 2.7672 1.1465 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4832 1.8171 3.0093 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5858 0.3058 2.9533 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6824 0.2698 1.7912 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1847 1.4069 0.5471 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9517 -1.3705 0.8746 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5180 -0.2117 -0.4150 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7894 0.1298 -0.9708 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2800 -1.1611 0.2737 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3715 -1.6639 -2.0955 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8743 -2.7871 -0.8071 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9511 -3.3208 -2.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0696 -3.0080 -1.5263 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7741 -2.2935 -3.8491 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3456 -1.2711 -3.9730 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3073 0.4774 -2.4926 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4382 -0.9924 -0.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6945 -1.3754 -2.0972 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0378 1.0306 -2.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7755 1.4365 -1.2448 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7900 -1.3472 0.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9797 -0.0417 2.2191 H 0 0 0 0 0 0 0 0 0 0 0 0 15.3794 0.0037 1.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6164 -0.2996 -0.3750 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4768 -1.5701 0.8663 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0357 -0.1513 -4.6925 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3457 1.2551 3.1552 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2641 -1.9425 0.0559 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 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 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 19 24 1 0 24 25 1 0 25 26 1 0 26 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 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 2 0 40 44 1 0 35 45 1 0 25 46 1 0 13 47 1 0 18 14 1 0 42 38 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 0 2 52 1 0 3 53 1 0 3 54 1 0 4 55 1 0 4 56 1 0 5 57 1 0 5 58 1 0 6 59 1 0 6 60 1 0 7 61 1 0 7 62 1 0 8 63 1 0 8 64 1 0 9 65 1 0 9 66 1 0 10 67 1 0 10 68 1 0 11 69 1 0 11 70 1 0 12 71 1 0 12 72 1 0 13 73 1 1 14 74 1 1 15 75 1 0 15 76 1 0 16 77 1 0 16 78 1 0 17 79 1 6 19 80 1 1 23 81 1 0 23 82 1 0 23 83 1 0 24 84 1 0 24 85 1 0 25 86 1 1 26 87 1 0 26 88 1 0 27 89 1 0 27 90 1 0 28 91 1 0 28 92 1 0 29 93 1 0 29 94 1 0 30 95 1 0 30 96 1 0 31 97 1 0 31 98 1 0 32 99 1 0 32100 1 0 33101 1 0 33102 1 0 34103 1 0 34104 1 0 35105 1 0 36106 1 0 36107 1 0 37108 1 0 37109 1 0 39110 1 0 40111 1 0 44112 1 0 44113 1 0 44114 1 0 45115 1 0 46116 1 0 47117 1 0 M END

Standard InCHIKey	BIODFBOSASJNMO-QLRBQNDPSA-N
Standard InCHI	InChI=1S/C39H70O8/c1-4-5-6-7-8-9-10-14-17-20-23-35(43)36-26-27-37(47-36)38(46-31(3)40)29-34(42)22-19-16-13-11-12-15-18-21-33(41)25-24-32-28-30(2)45-39(32)44/h28,30,33-38,41-43H,4-27,29H2,1-3H3/t30?,33?,34-,35-,36-,37-,38-/m1/s1
SMILES	CCCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@H](OC(=O)C)C[C@@H](CCCCCCCCCC(CCC1=CC(OC1=O)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.51	Volume:	728.399 ? Van der Waals volume.
Dense:	0.915	LogP:	6.459 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.163 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.935 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	30.0	Rigid Bonds:	12.0
TPSA:	122.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.054	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.757	Fsp³:	0.897
MCE-18:	34.162 ? 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:	0.918	Fluc inhibitor:	0.006 ? 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:	0.008 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.466	Promiscuous compounds:	0.168

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.249	MDCK Permeability:	-4.839
Pgp-inhibitor:	0.004	Pgp-substrate:	0.829
PAMPA:	0.054 ? 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):	0.936
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.88
Plasma Protein Binding (PPB):	96.994%	Volume Distribution (VD):	0.511
Fu:	2.887% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.631
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.49
BSEP inhibitor:	0.827

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.087	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.419	CYP2C9-substrate:	0.314
CYP2D6-inhibitor:	0.092	CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.991
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.831
HLM stability:	0.437 ? 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):

5.515

Half-life (T1/2):

1.031

ADMET: Toxicity

hERG Blockers:	0.468	hERG Blockers (10um):	0.854
Human Hepatotoxicity (H-HT):	0.569	Drug-induced Liver Injury (DILI):	0.03
AMES Toxicity:	0.017	Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.662	Skin Sensitization:	1.0
Carcinogencity:	0.106	Eye Corrosion:	0.013
Eye Irritation:	0.622	Respiratory Toxicity:	0.959
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.86
Hematotoxicity:	0.057	Drug-induced Nephrotoxicity:	0.897
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.056
A549 Cytotoxicity:	0.939	Hek293 Cytotoxicity:	0.224
BCF:	0.74 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.337 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.745 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.174 ? 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
NPO33316	ampelocissus sp.	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18177007]
NPO11129	Uvaria boniana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11129	Uvaria boniana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11129	Uvaria boniana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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
GI50	6

Activity Type	# Activity
Cell line	6

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
NPT1081	Cell line	BXPC-3	Homo sapiens	GI50	=	1.3	ug.mL-1	PMID[18177007]
NPT83	Cell line	MCF7	Homo sapiens	GI50	=	0.0022	ug.mL-1	PMID[18177007]
NPT395	Cell line	SF-268	Homo sapiens	GI50	=	1.4	ug.mL-1	PMID[18177007]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	=	1.0	ug.mL-1	PMID[18177007]
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	=	0.0013	ug.mL-1	PMID[18177007]
NPT90	Cell line	DU-145	Homo sapiens	GI50	=	0.0093	ug.mL-1	PMID[18177007]

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 NPC89001 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	18566
0.1-0.2	28576
0.2-0.3	2422
0.3-0.4	68
0.4-0.5	34
0.5-0.6	68
0.6-0.7	63
0.7-0.8	0
0.8-0.85	4
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.902	High Similarity	NPC120398
0.902	High Similarity	NPC471567
0.8776	High Similarity	NPC473649
0.8776	High Similarity	NPC154097
0.8776	High Similarity	NPC159750
0.8776	High Similarity	NPC73248
0.8776	High Similarity	NPC470401
0.86	High Similarity	NPC604764
0.8039	Intermediate Similarity	NPC473156
0.8039	Intermediate Similarity	NPC282815
0.8039	Intermediate Similarity	NPC600956
0.8039	Intermediate Similarity	NPC610454
0.7885	Intermediate Similarity	NPC473671
0.7885	Intermediate Similarity	NPC475268
0.7885	Intermediate Similarity	NPC470400
0.7885	Intermediate Similarity	NPC77871
0.7885	Intermediate Similarity	NPC9678
0.7885	Intermediate Similarity	NPC319036
0.7885	Intermediate Similarity	NPC605867
0.78	Intermediate Similarity	NPC100921
0.78	Intermediate Similarity	NPC477018
0.7736	Intermediate Similarity	NPC132940
0.7593	Intermediate Similarity	NPC20533
0.7451	Intermediate Similarity	NPC25764
0.7451	Intermediate Similarity	NPC235809
0.7451	Intermediate Similarity	NPC39279
0.7451	Intermediate Similarity	NPC39167
0.7451	Intermediate Similarity	NPC292809
0.7451	Intermediate Similarity	NPC202055
0.7451	Intermediate Similarity	NPC606804
0.7451	Intermediate Similarity	NPC607425
0.7451	Intermediate Similarity	NPC608574
0.7358	Intermediate Similarity	NPC93794
0.7358	Intermediate Similarity	NPC473504
0.7358	Intermediate Similarity	NPC81778
0.7358	Intermediate Similarity	NPC40066
0.7358	Intermediate Similarity	NPC600524
0.7358	Intermediate Similarity	NPC608355
0.717	Intermediate Similarity	NPC81045
0.717	Intermediate Similarity	NPC39754
0.717	Intermediate Similarity	NPC171135
0.717	Intermediate Similarity	NPC61257
0.717	Intermediate Similarity	NPC320569
0.717	Intermediate Similarity	NPC133730
0.717	Intermediate Similarity	NPC191929
0.717	Intermediate Similarity	NPC100454
0.717	Intermediate Similarity	NPC242364
0.717	Intermediate Similarity	NPC172821
0.717	Intermediate Similarity	NPC274446
0.717	Intermediate Similarity	NPC485251
0.717	Intermediate Similarity	NPC151403
0.717	Intermediate Similarity	NPC261952
0.717	Intermediate Similarity	NPC605171
0.7115	Intermediate Similarity	NPC475159
0.7115	Intermediate Similarity	NPC131002
0.7115	Intermediate Similarity	NPC473780
0.7115	Intermediate Similarity	NPC604521
0.7091	Intermediate Similarity	NPC42598
0.6964	Remote Similarity	NPC309211
0.6964	Remote Similarity	NPC477010
0.6909	Remote Similarity	NPC219652
0.6909	Remote Similarity	NPC473840
0.6852	Remote Similarity	NPC156804
0.6667	Remote Similarity	NPC485250
0.6667	Remote Similarity	NPC602738
0.6667	Remote Similarity	NPC605396
0.661	Remote Similarity	NPC477014
0.661	Remote Similarity	NPC477013
0.6607	Remote Similarity	NPC25703
0.6538	Remote Similarity	NPC73310
0.6538	Remote Similarity	NPC473529
0.6538	Remote Similarity	NPC180363
0.6538	Remote Similarity	NPC94875
0.6538	Remote Similarity	NPC11332
0.6538	Remote Similarity	NPC145914
0.6538	Remote Similarity	NPC601174
0.6538	Remote Similarity	NPC601403
0.6538	Remote Similarity	NPC603568
0.6538	Remote Similarity	NPC604330
0.6538	Remote Similarity	NPC608300
0.6538	Remote Similarity	NPC611200
0.6538	Remote Similarity	NPC611571
0.6508	Remote Similarity	NPC477017
0.6508	Remote Similarity	NPC477016
0.65	Remote Similarity	NPC239517
0.6481	Remote Similarity	NPC107986
0.6481	Remote Similarity	NPC223871
0.6481	Remote Similarity	NPC231009
0.6481	Remote Similarity	NPC103284
0.6481	Remote Similarity	NPC110710
0.6481	Remote Similarity	NPC1083
0.6481	Remote Similarity	NPC82795
0.6481	Remote Similarity	NPC286338
0.6481	Remote Similarity	NPC603931
0.6481	Remote Similarity	NPC604237
0.6441	Remote Similarity	NPC169511
0.6441	Remote Similarity	NPC287164
0.6441	Remote Similarity	NPC234077
0.6441	Remote Similarity	NPC473995
0.6429	Remote Similarity	NPC163093
0.6379	Remote Similarity	NPC329838
0.6364	Remote Similarity	NPC488253
0.6364	Remote Similarity	NPC473669
0.6364	Remote Similarity	NPC488251
0.6296	Remote Similarity	NPC606043
0.629	Remote Similarity	NPC473905
0.625	Remote Similarity	NPC232555
0.625	Remote Similarity	NPC171174
0.625	Remote Similarity	NPC114694
0.625	Remote Similarity	NPC485248
0.625	Remote Similarity	NPC142117
0.625	Remote Similarity	NPC480249
0.625	Remote Similarity	NPC485249
0.625	Remote Similarity	NPC240695
0.6182	Remote Similarity	NPC329829
0.6167	Remote Similarity	NPC258068
0.6167	Remote Similarity	NPC476583
0.614	Remote Similarity	NPC488632
0.614	Remote Similarity	NPC477011
0.6129	Remote Similarity	NPC473520
0.6129	Remote Similarity	NPC91067
0.5965	Remote Similarity	NPC182383
0.5938	Remote Similarity	NPC473663
0.5938	Remote Similarity	NPC473723
0.5938	Remote Similarity	NPC475173
0.5932	Remote Similarity	NPC178215
0.5862	Remote Similarity	NPC134865
0.5862	Remote Similarity	NPC103523
0.5862	Remote Similarity	NPC144415
0.5862	Remote Similarity	NPC488627
0.5862	Remote Similarity	NPC488631
0.5862	Remote Similarity	NPC607439
0.5862	Remote Similarity	NPC608157
0.5833	Remote Similarity	NPC488250
0.5763	Remote Similarity	NPC280621
0.5763	Remote Similarity	NPC48338
0.5763	Remote Similarity	NPC241360
0.5763	Remote Similarity	NPC293136
0.5763	Remote Similarity	NPC488628
0.5738	Remote Similarity	NPC69082
0.5738	Remote Similarity	NPC488249
0.5667	Remote Similarity	NPC473687
0.5667	Remote Similarity	NPC204686
0.5667	Remote Similarity	NPC219498
0.5667	Remote Similarity	NPC65930
0.5667	Remote Similarity	NPC308412
0.5667	Remote Similarity	NPC134885
0.5667	Remote Similarity	NPC488247
0.5667	Remote Similarity	NPC210218
0.5667	Remote Similarity	NPC488248
0.5625	Remote Similarity	NPC280612
0.5593	Remote Similarity	NPC47937
0.5574	Remote Similarity	NPC20621
0.5574	Remote Similarity	NPC318963
0.5574	Remote Similarity	NPC605101
0.5556	Remote Similarity	NPC488623
0.5556	Remote Similarity	NPC488624
0.5556	Remote Similarity	NPC233551
0.5556	Remote Similarity	NPC40376
0.5556	Remote Similarity	NPC21208
0.5556	Remote Similarity	NPC488629
0.5538	Remote Similarity	NPC477015
0.55	Remote Similarity	NPC480079
0.5484	Remote Similarity	NPC473478
0.5484	Remote Similarity	NPC473651
0.5484	Remote Similarity	NPC20339
0.5484	Remote Similarity	NPC66346
0.5484	Remote Similarity	NPC477012
0.5472	Remote Similarity	NPC608138
0.5397	Remote Similarity	NPC283085
0.5397	Remote Similarity	NPC130359
0.5397	Remote Similarity	NPC14901
0.5323	Remote Similarity	NPC329615
0.5323	Remote Similarity	NPC134807
0.5263	Remote Similarity	NPC112685
0.5238	Remote Similarity	NPC473707
0.5185	Remote Similarity	NPC609415
0.5172	Remote Similarity	NPC480072
0.5156	Remote Similarity	NPC231096
0.5156	Remote Similarity	NPC475581
0.5156	Remote Similarity	NPC62118
0.5156	Remote Similarity	NPC132496
0.5156	Remote Similarity	NPC107717
0.5156	Remote Similarity	NPC488252
0.5152	Remote Similarity	NPC488630
0.5152	Remote Similarity	NPC488625
0.5152	Remote Similarity	NPC488626
0.5077	Remote Similarity	NPC480082
0.5075	Remote Similarity	NPC253801

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC89001 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6804
0.1-0.2	2306
0.2-0.3	40
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data