NPASS Compound

Natural Product: NPC146787

Natural Product ID	NPC146787
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OCEDEAQHBIGPTE-AOJBDTRXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

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 119126 0 0 0 0 0 0 0 0999 V2000 11.2874 -2.6101 -1.7005 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9259 -1.2465 -1.4876 C 0 0 2 0 0 0 0 0 0 0 0 0 13.1207 -1.3489 -0.5665 C 0 0 2 0 0 0 0 0 0 0 0 0 12.9491 -0.3565 0.5901 C 0 0 2 0 0 0 0 0 0 0 0 0 11.5668 -0.7343 1.1500 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5852 -0.2408 0.1347 C 0 0 1 0 0 0 0 0 0 0 0 0 11.0327 -0.2581 -1.1573 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3273 -0.7636 0.1738 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3118 0.0986 0.5205 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6055 -0.4700 1.7069 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3616 0.1084 2.9422 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3185 -0.1377 1.8942 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4586 0.0775 0.8832 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1368 1.0763 -0.0767 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3143 0.2631 -0.6149 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8472 -1.0000 -1.0200 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2891 0.6304 1.3923 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2129 0.0127 0.7477 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3947 1.0353 -0.0072 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0715 0.6528 -1.4086 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3077 1.4067 0.7129 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3317 0.4541 0.9378 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9718 -0.9413 0.9753 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3499 -0.8134 1.6238 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2908 -0.3091 2.9077 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5749 0.4954 -0.0676 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8877 0.6271 0.2533 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3993 2.0573 -0.0386 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8557 2.0085 0.4405 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6209 1.4471 -0.7485 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8081 2.6276 -1.6924 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7759 0.3574 -1.3749 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6825 -0.7339 -1.9034 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9453 -0.2348 -2.5295 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7559 0.5980 -1.5680 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9160 0.8102 -0.3455 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7399 1.6505 0.6084 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8474 0.7174 1.0657 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7536 0.2650 -0.0220 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8830 1.2745 -0.1109 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2302 -1.1258 0.3494 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2414 -1.2902 1.3484 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8467 -0.4277 2.1162 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8558 -1.1106 3.0189 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7388 -2.4550 2.6321 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8000 -2.6432 1.6547 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4696 -3.7395 1.1163 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6173 -1.6874 -1.0315 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2770 -1.3828 -1.7542 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1140 0.0759 -1.3777 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9478 0.7512 -2.3105 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5695 -0.8806 -1.6280 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8593 -0.3024 -0.3574 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8808 0.9158 -0.0053 O 0 0 0 0 0 0 0 0 0 0 0 0 14.3218 -1.1210 -1.1861 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1059 -3.1165 -0.7250 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9808 -3.2186 -2.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3568 -2.4904 -2.2829 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3464 -0.9730 -2.4921 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0926 -2.3531 -0.0977 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7388 -0.4695 1.3234 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4873 -0.1384 2.1059 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5941 -1.8042 1.3168 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4552 0.8594 0.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6652 1.1158 0.7841 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7657 -1.5903 1.7828 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7131 0.1530 3.8145 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2695 -0.4458 3.1540 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6513 1.1567 2.6663 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2221 -0.7744 0.2050 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4345 1.2128 -0.9172 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4755 1.9787 0.4124 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7001 0.7777 -1.4867 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0189 -1.1580 -1.9690 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6049 -0.7087 -0.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0909 1.9661 -0.1324 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0142 0.6076 -1.6421 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4894 -0.3592 -1.7014 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5143 1.3704 -2.1738 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1090 0.5630 1.9563 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1247 -1.3364 -0.0363 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3498 -1.5858 1.6107 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6992 -1.8677 1.7276 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8577 0.4753 3.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9702 0.5861 1.3720 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3203 2.2308 -1.1043 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8030 2.8044 0.4769 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1816 3.0385 0.7042 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9624 1.3340 1.2986 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7163 3.2054 -1.4183 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7552 2.3512 -2.7559 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9604 3.3669 -1.5647 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2550 0.7911 -2.2268 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8625 -1.4993 -1.0996 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0831 -1.2734 -2.6810 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6832 0.2864 -3.4694 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5030 -1.1398 -2.8675 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8209 1.6182 -2.0577 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6660 -0.1279 0.1788 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2433 2.4907 0.0850 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1600 1.9374 1.4893 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4298 1.2047 1.8607 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3054 -0.1540 1.5463 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7761 1.8235 -1.0835 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8820 0.8597 -0.0823 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8090 2.0588 0.6990 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3416 -1.7685 0.6368 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7327 0.6597 2.2188 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8581 -0.6852 2.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5157 -0.9995 4.0570 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8693 -2.7320 -1.0323 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4928 -1.5556 -2.8198 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4860 -2.0241 -1.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5057 1.5628 -2.6570 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5984 -0.8845 -2.5957 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3947 -1.1606 -0.9274 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5377 -0.7985 0.3775 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3681 1.5464 0.5612 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8450 -0.4765 -0.6837 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 13 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 22 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 6 30 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 1 0 39 40 1 6 39 41 1 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 2 0 41 48 1 0 48 49 1 0 49 50 1 0 50 51 1 6 48 52 1 0 32 53 1 0 4 54 1 0 3 55 1 0 7 2 1 0 15 9 1 0 24 18 1 0 53 27 1 0 36 30 1 0 50 39 1 0 50 35 1 0 46 42 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 6 3 60 1 1 4 61 1 1 5 62 1 0 5 63 1 0 6 64 1 1 9 65 1 1 10 66 1 6 11 67 1 0 11 68 1 0 11 69 1 0 13 70 1 6 14 71 1 0 14 72 1 0 15 73 1 6 16 74 1 0 18 75 1 6 19 76 1 6 20 77 1 0 20 78 1 0 20 79 1 0 22 80 1 1 23 81 1 0 23 82 1 0 24 83 1 1 25 84 1 0 27 85 1 1 28 86 1 0 28 87 1 0 29 88 1 0 29 89 1 0 31 90 1 0 31 91 1 0 31 92 1 0 32 93 1 6 33 94 1 0 33 95 1 0 34 96 1 0 34 97 1 0 35 98 1 6 36 99 1 1 37100 1 0 37101 1 0 38102 1 0 38103 1 0 40104 1 0 40105 1 0 40106 1 0 41107 1 1 43108 1 0 44109 1 0 44110 1 0 48111 1 1 49112 1 0 49113 1 0 51114 1 0 52115 1 0 53116 1 0 53117 1 0 54118 1 0 55119 1 0 M END

Standard InCHIKey	OCEDEAQHBIGPTE-AOJBDTRXSA-N
Standard InCHI	InChI=1S/C41H64O14/c1-19-35(46)27(42)15-32(50-19)54-37-21(3)52-33(17-29(37)44)55-36-20(2)51-31(16-28(36)43)53-23-8-11-39(4)22(14-23)6-7-26-25(39)9-12-40(5)34(24-10-13-49-38(24)47)30(45)18-41(26,40)48/h10,19-23,25-37,42-46,48H,6-9,11-18H2,1-5H3/t19-,20-,21-,22-,23+,25+,26-,27+,28+,29+,30+,31+,32+,33+,34+,35-,36-,37-,39+,40-,41+/m1/s1
SMILES	C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]1[C@@H](C)O[C@H](C[C@@H]1O)O[C@@H]1[C@@H](C)O[C@H](C[C@@H]1O)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](C4=CCOC4=O)[C@H](C[C@]32O)O)C1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	780.43	Volume:	767.03 ? Van der Waals volume.
Dense:	1.017	LogP:	1.86 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.525 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.483 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	44.0
TPSA:	203.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	6.0	Rings:	8.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.162	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.162	Fsp³:	0.927
MCE-18:	150.278 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.752	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? 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:	0.304	Promiscuous compounds:	0.586

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.64	MDCK Permeability:	-5.235
Pgp-inhibitor:	0.011	Pgp-substrate:	0.978
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):	0.002
20% Bioavailability (F20%):	0.323	30% Bioavailability (F30%):	0.239
50% Bioavailability (F50%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.942
Plasma Protein Binding (PPB):	59.909%	Volume Distribution (VD):	-0.592
Fu:	32.235% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.887	BCRP inhibitor:	0.005
BSEP inhibitor:	0.976

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.048	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.976	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.964
HLM stability:	0.325 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.642

Half-life (T1/2):

4.417

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.608
Human Hepatotoxicity (H-HT):	0.26	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.988	Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.976	Skin Sensitization:	1.0
Carcinogencity:	0.726	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.938
Drug-induced Neurotoxicity:	0.13	Ototoxicity:	0.982
Hematotoxicity:	0.907	Drug-induced Nephrotoxicity:	0.954
Genotoxicity:	0.892	RPMI-8226 Immunitoxicity:	0.609
A549 Cytotoxicity:	0.979	Hek293 Cytotoxicity:	0.829
BCF:	0.501 ? 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:	3.266 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.88 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.932 ? 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
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.lwt.2014.11.023]
NPO12474	Cordyline fruticosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27168	Atropa belladona	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18180	Erysimum repandum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27168	Atropa belladona	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19093	Streptomyces aburaviensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19175	Iguana iguana	Species	Iguanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19441	Strychnos splendens	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12474	Cordyline fruticosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18180	Erysimum repandum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17635	Aria arguta	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18930	Rubus coreanus	Species	Rosaceae	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 NPC146787 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	18634
0.1-0.2	27314
0.2-0.3	3620
0.3-0.4	158
0.4-0.5	100
0.5-0.6	29
0.6-0.7	2
0.7-0.8	1
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
0.8375	Intermediate Similarity	NPC193893
0.7412	Intermediate Similarity	NPC72260
0.6742	Remote Similarity	NPC173555
0.6588	Remote Similarity	NPC471633
0.596	Remote Similarity	NPC475219
0.5889	Remote Similarity	NPC99080
0.5876	Remote Similarity	NPC55532
0.5728	Remote Similarity	NPC120390
0.5728	Remote Similarity	NPC74259
0.5686	Remote Similarity	NPC475590
0.5612	Remote Similarity	NPC231518
0.5612	Remote Similarity	NPC488944
0.5556	Remote Similarity	NPC208193
0.5543	Remote Similarity	NPC479356
0.5543	Remote Similarity	NPC479355
0.5495	Remote Similarity	NPC99620
0.5288	Remote Similarity	NPC479360
0.5288	Remote Similarity	NPC479359
0.5248	Remote Similarity	NPC125077
0.5234	Remote Similarity	NPC117445
0.5234	Remote Similarity	NPC308262
0.5161	Remote Similarity	NPC473852
0.5158	Remote Similarity	NPC84949
0.5158	Remote Similarity	NPC480562
0.5158	Remote Similarity	NPC74945
0.5158	Remote Similarity	NPC31354
0.5158	Remote Similarity	NPC69576
0.51	Remote Similarity	NPC236973
0.5053	Remote Similarity	NPC5311
0.5051	Remote Similarity	NPC103534
0.5051	Remote Similarity	NPC44899
0.5051	Remote Similarity	NPC304260
0.5051	Remote Similarity	NPC29639

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC146787 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6865
0.1-0.2	2191
0.2-0.3	79
0.3-0.4	5
0.4-0.5	2
0.5-0.6	5
0.6-0.7	2
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7412	Intermediate Similarity	NPD8294	Phase 4
0.6742	Remote Similarity	NPD8296	Phase 4
0.6211	Remote Similarity	NPD8377	Phase 4
0.587	Remote Similarity	NPD8380	Approved
0.5761	Remote Similarity	NPD8335	Phase 4
0.5657	Remote Similarity	NPD8378	Pre-clinical
0.5657	Remote Similarity	NPD8379	Approved
0.5612	Remote Similarity	NPD8033	Approved

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