NPASS Compound

Natural Product: NPC142012

Natural Product ID	NPC142012
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WWEXTVPYKGAYFK-CCYMNORKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21579927
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 125131 0 0 0 0 0 0 0 0999 V2000 3.0651 -0.8277 0.6902 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3587 0.4618 0.9222 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7510 0.9033 2.3415 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8537 0.3785 0.9538 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3940 -0.5266 2.0473 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0384 -0.1268 2.3318 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8725 -0.2491 1.0972 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1341 -1.7238 0.9248 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2840 0.4081 -0.1310 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1458 0.1686 -1.3104 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5859 0.6249 -1.1027 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0990 0.0528 0.1654 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4391 0.3873 0.6294 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3468 0.5472 2.1463 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9420 0.1078 2.5095 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1940 0.5098 1.2856 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0087 1.9792 1.3657 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5605 -0.5790 0.3881 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2861 -1.9619 0.9980 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9373 -0.8046 -1.0261 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2903 -1.4811 -1.1531 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3382 -0.9146 -0.2755 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7817 0.1679 0.6042 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8005 0.3246 1.7505 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8547 1.4653 -0.1733 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5944 -0.0805 1.1818 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9489 -1.8636 0.5521 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6746 -1.3916 -2.5107 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2435 0.1072 -2.2516 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1796 0.1653 -0.3595 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4602 -1.1798 -0.9733 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6847 1.2029 -1.3218 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7214 2.1364 -0.8104 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8468 1.4943 -0.0212 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7479 1.0006 -0.9816 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9146 1.6922 -1.0205 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2039 0.9674 -0.8665 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1755 2.0580 -0.3451 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2918 3.0353 -1.4837 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9209 3.4869 -1.8899 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0243 4.4146 -3.0839 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5034 3.7564 -4.1968 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0490 2.4480 -2.2152 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0194 4.1399 -1.0840 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3509 1.5529 0.1179 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1730 -0.1372 -0.0829 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6685 -1.2933 -0.6671 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8830 -1.8775 -0.0670 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9866 -3.3606 -0.4607 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7848 -4.1122 0.0963 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6164 -3.1325 0.2154 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7043 -2.2543 -0.8880 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4647 -5.2451 -0.6282 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1228 -3.9585 0.0677 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0833 -1.3277 -0.5821 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4751 -1.7326 0.8032 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5303 -0.8103 -0.3395 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9564 -0.9555 1.3760 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6902 1.4916 2.3178 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9742 0.0103 2.9615 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9589 1.5221 2.7989 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5303 1.4195 1.2785 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5433 -1.5886 1.8848 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9594 -0.2444 2.9718 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0340 0.8234 2.8424 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4205 -0.8846 3.0656 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2876 -2.3250 1.3815 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0188 -2.0988 1.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2164 -2.0794 -0.0945 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3521 1.5202 0.0717 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1772 -0.8699 -1.6948 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7885 0.7764 -2.1655 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7101 1.7161 -1.2369 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0224 -1.0504 0.0696 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7523 1.3468 0.1580 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0435 -0.0636 2.7120 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5469 1.6032 2.4409 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8425 -0.8948 2.8731 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6405 0.7849 3.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7436 2.4674 2.0768 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0655 2.5641 0.4603 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0219 2.2630 1.8361 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2960 -2.4175 1.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7753 -2.6155 0.2609 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8017 -1.9230 1.9678 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9126 0.0681 -1.6777 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2276 -1.5831 -1.4408 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1966 -2.5715 -0.9488 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1550 -0.4745 -0.8895 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4251 -0.1548 2.6818 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9334 1.4001 1.9954 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7958 -0.0710 1.4578 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9586 1.2520 -1.2781 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7743 2.0556 0.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0062 2.1463 0.0374 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5947 -1.7920 1.4786 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2439 -2.0800 -3.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7270 0.3164 -3.0545 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4666 -1.1566 -1.4150 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3789 -2.0315 -0.3118 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2212 -1.2648 -1.8706 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1793 1.8264 -1.6484 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1624 0.7196 -2.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1317 2.8125 -1.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2069 2.8270 -0.0795 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3385 2.3371 0.5243 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8488 2.4617 -0.1822 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6066 0.7683 -1.8945 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5958 2.5783 0.4655 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8268 2.5599 -2.3552 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4685 4.0428 -1.0516 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0042 4.7892 -3.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6615 5.2805 -2.8424 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7841 3.5171 -4.8313 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0432 4.1825 -0.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2750 1.4624 1.1147 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9764 -0.9523 -1.7106 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8869 -1.8821 1.0455 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9915 -3.5072 -1.5437 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0462 -4.4181 1.1221 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6563 -3.6518 0.1858 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6908 -2.5630 1.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2034 -4.9452 -1.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6397 -4.4613 -0.5970 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7962 -1.9736 -0.3410 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 7 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 1 13 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 23 25 1 0 23 26 1 0 22 27 1 0 21 28 1 0 11 29 1 0 9 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 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 38 45 1 0 37 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 48 55 1 0 34 2 1 0 43 36 1 0 52 47 1 0 30 4 1 0 16 7 1 0 26 18 1 0 16 12 1 0 1 56 1 0 1 57 1 0 1 58 1 0 3 59 1 0 3 60 1 0 3 61 1 0 4 62 1 1 5 63 1 0 5 64 1 0 6 65 1 0 6 66 1 0 8 67 1 0 8 68 1 0 8 69 1 0 9 70 1 1 10 71 1 0 10 72 1 0 11 73 1 1 12 74 1 6 13 75 1 6 14 76 1 0 14 77 1 0 15 78 1 0 15 79 1 0 17 80 1 0 17 81 1 0 17 82 1 0 19 83 1 0 19 84 1 0 19 85 1 0 20 86 1 0 20 87 1 0 21 88 1 1 22 89 1 6 24 90 1 0 24 91 1 0 24 92 1 0 25 93 1 0 25 94 1 0 25 95 1 0 27 96 1 0 28 97 1 0 29 98 1 0 31 99 1 0 31100 1 0 31101 1 0 32102 1 0 32103 1 0 33104 1 0 33105 1 0 34106 1 1 36107 1 1 37108 1 6 38109 1 1 39110 1 6 40111 1 1 41112 1 0 41113 1 0 42114 1 0 44115 1 0 45116 1 0 47117 1 6 48118 1 1 49119 1 6 50120 1 1 51121 1 0 51122 1 0 53123 1 0 54124 1 0 55125 1 0 M END

Standard InCHIKey	WWEXTVPYKGAYFK-CCYMNORKSA-N
Standard InCHI	InChI=1S/C41H70O14/c1-36(2)24-10-14-39(6)25(15-20(43)27-19(9-13-40(27,39)7)41(8)16-21(44)33(50)37(3,4)55-41)38(24,5)12-11-26(36)53-35-32(30(48)29(47)23(17-42)52-35)54-34-31(49)28(46)22(45)18-51-34/h19-35,42-50H,9-18H2,1-8H3/t19-,20+,21-,22+,23+,24-,25+,26-,27-,28-,29+,30-,31+,32+,33+,34-,35-,38-,39+,40+,41-/m0/s1
SMILES	CC1(C)[C@@H]2CC[C@]3(C)[C@H](C[C@H]([C@@H]4[C@H](CC[C@@]34C)[C@]3(C)C[C@@H]([C@H](C(C)(C)O3)O)O)O)[C@@]2(C)CC[C@@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	786.48	Volume:	780.86 ? Van der Waals volume.
Dense:	1.007	LogP:	2.473 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.921 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.537 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	38.0
TPSA:	228.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.171	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.031	Fsp³:	1.0
MCE-18:	155.707 ? 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:	0.771	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.186	Promiscuous compounds:	0.022

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.19	MDCK Permeability:	-5.039
Pgp-inhibitor:	0.005	Pgp-substrate:	0.714
PAMPA:	0.997 ? 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):	0.054
20% Bioavailability (F20%):	0.634	30% Bioavailability (F30%):	0.952
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022	MRP1:	0.603
Plasma Protein Binding (PPB):	78.027%	Volume Distribution (VD):	-0.398
Fu:	14.772% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.008
BSEP inhibitor:	0.048

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.005	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.009	CYP3A4-substrate:	0.009
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.314
HLM stability:	0.863 ? 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):

0.564

Half-life (T1/2):

2.465

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.04
Human Hepatotoxicity (H-HT):	0.398	Drug-induced Liver Injury (DILI):	0.173
AMES Toxicity:	0.833	Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.012	Skin Sensitization:	1.0
Carcinogencity:	0.088	Eye Corrosion:	0.0
Eye Irritation:	0.008	Respiratory Toxicity:	0.009
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.993
Hematotoxicity:	0.57	Drug-induced Nephrotoxicity:	0.977
Genotoxicity:	0.038	RPMI-8226 Immunitoxicity:	0.241
A549 Cytotoxicity:	0.732	Hek293 Cytotoxicity:	0.481
BCF:	1.153 ? 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:	3.243 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.356 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.627 ? 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
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20104880]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342101]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25895106]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	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 NPC142012 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	24336
0.1-0.2	21893
0.2-0.3	2710
0.3-0.4	721
0.4-0.5	154
0.5-0.6	36
0.6-0.7	7
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	Natural Product ID
0.6979	Remote Similarity	NPC159005
0.6804	Remote Similarity	NPC14946
0.6804	Remote Similarity	NPC63368
0.6739	Remote Similarity	NPC194842
0.6484	Remote Similarity	NPC208477
0.6458	Remote Similarity	NPC208650
0.6327	Remote Similarity	NPC220427
0.5978	Remote Similarity	NPC472897
0.5978	Remote Similarity	NPC472896
0.5962	Remote Similarity	NPC135369
0.587	Remote Similarity	NPC159036
0.5851	Remote Similarity	NPC472987
0.578	Remote Similarity	NPC146868
0.5776	Remote Similarity	NPC488293
0.5769	Remote Similarity	NPC246124
0.5745	Remote Similarity	NPC312553
0.5745	Remote Similarity	NPC8039
0.5745	Remote Similarity	NPC120123
0.5741	Remote Similarity	NPC241381
0.5727	Remote Similarity	NPC488294
0.5657	Remote Similarity	NPC210759
0.5612	Remote Similarity	NPC269627
0.5567	Remote Similarity	NPC69737
0.5545	Remote Similarity	NPC234160
0.5495	Remote Similarity	NPC488292
0.5437	Remote Similarity	NPC472988
0.5437	Remote Similarity	NPC38217
0.5435	Remote Similarity	NPC31907
0.5431	Remote Similarity	NPC488291
0.5408	Remote Similarity	NPC181467
0.5333	Remote Similarity	NPC160816
0.5288	Remote Similarity	NPC476360
0.5288	Remote Similarity	NPC476361
0.5248	Remote Similarity	NPC304011
0.5238	Remote Similarity	NPC488561
0.5189	Remote Similarity	NPC469946
0.514	Remote Similarity	NPC305418
0.5138	Remote Similarity	NPC472718
0.5102	Remote Similarity	NPC45959
0.5098	Remote Similarity	NPC472715
0.5098	Remote Similarity	NPC236753
0.5094	Remote Similarity	NPC65167
0.5091	Remote Similarity	NPC6931

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC142012 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7558
0.1-0.2	1541
0.2-0.3	47
0.3-0.4	4
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