NPASS Compound

Natural Product: NPC475287

Natural Product ID	NPC475287
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Methyl (4As,6Ar,6As,6Br,8Ar,10S,12Ar,14Bs)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-(Hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-3,5-Dihydroxy-6-Methyloxan-2-Yl]Oxy-4,5-Dihydroxyoxan-2-Yl]Oxy-2,2,6A,6B,9,9,12A-Heptamethyl-1,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydropicene-4A-Carboxylate
IUPAC Name	methyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL502879
PubChem CID	10629958
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 163171 0 0 0 0 0 0 0 0999 V2000 1.9073 -1.0112 3.0661 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5223 0.0860 2.1798 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6955 -0.5492 1.4668 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4113 0.5190 0.6819 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4019 1.6595 0.4861 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0783 1.0006 0.1498 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5029 0.4891 1.3389 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1323 0.0989 -0.8456 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4469 0.2741 -1.9997 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3250 0.2199 -3.2453 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4457 -0.3203 -4.3575 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1641 -1.8016 -4.0900 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0588 -1.9911 -2.7079 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4790 -0.8883 -2.1309 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0255 -1.1269 -0.8566 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3823 -0.9127 -0.7640 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6259 0.2614 0.1970 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0970 0.5495 -0.0433 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9939 -0.5736 0.4882 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3422 -1.9156 0.4989 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0172 -2.0874 -0.1291 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9846 -2.6341 0.8732 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0800 -3.1811 -1.2095 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2770 -3.0015 -0.0041 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6368 -2.6753 0.5774 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2197 -1.5826 -0.3041 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1576 -0.5618 -0.5194 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5802 0.7689 -0.9805 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0151 1.0673 -0.6723 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9145 0.2440 -0.1987 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5761 -1.1776 0.0999 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9822 -1.3470 1.5397 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4321 -0.0975 2.2329 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5620 0.6641 1.5910 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2746 0.7610 0.0934 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3988 0.2587 -0.7277 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5967 1.1687 -0.3138 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9667 0.8907 1.1036 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9204 0.1162 1.8546 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3579 2.5924 -0.6639 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7358 0.6632 -1.2057 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4846 2.0266 2.2415 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4076 2.4059 2.9545 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3621 2.8073 2.0071 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2850 4.0788 2.6104 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5748 -2.0496 -0.6840 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3585 -2.2866 -1.6752 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3671 -0.1421 1.8598 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1004 -0.2416 -5.5920 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3467 -0.7204 -3.0834 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8042 2.5612 -0.4764 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5760 0.9402 1.2890 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7199 0.7473 0.4805 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3680 2.1001 0.2901 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7350 1.9918 0.9849 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4669 0.9278 0.1854 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7782 -0.3766 0.4093 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5639 -0.1819 1.0188 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6431 -1.1993 -0.8415 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8568 -0.6642 -1.8190 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8191 0.9121 0.4428 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6506 1.2733 -0.5711 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6046 2.4059 -0.1560 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3831 1.9029 1.0373 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1239 0.4745 1.3778 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8738 -0.4452 0.2399 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4878 0.2126 -0.8891 O 0 0 0 0 0 0 0 0 0 0 0 0 14.1072 -1.2669 -0.1188 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8035 -2.1722 -1.1343 O 0 0 0 0 0 0 0 0 0 0 0 0 14.2989 0.0029 2.0215 O 0 0 0 0 0 0 0 0 0 0 0 0 14.7582 2.0934 0.8455 O 0 0 0 0 0 0 0 0 0 0 0 0 13.5125 2.5949 -1.2149 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3385 3.2201 0.8988 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5800 2.3158 -1.0513 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3064 -1.6427 0.7145 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8154 -0.9516 3.0996 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2919 -0.9474 4.1039 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1814 -2.0180 2.6889 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8322 0.8706 2.8848 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3784 -0.9128 2.2963 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6827 0.0910 -0.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3798 2.1953 1.4552 H 0 0 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0 0 0 0 0 0 0 8.5062 1.6622 2.0186 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3364 1.2246 -0.8745 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3904 -0.9631 1.1831 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6971 -1.3724 -1.2121 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2714 -2.2188 -0.5855 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0526 -1.1210 -2.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1416 1.5563 -1.5123 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0865 3.3201 0.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0953 2.5021 1.9519 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3138 0.4002 2.1515 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0484 -1.1515 0.5447 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3629 -1.8836 0.7724 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9316 -0.6309 -0.4416 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1305 -1.7999 -2.0038 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0268 -0.7490 2.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 15.1646 2.1871 1.7493 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3772 2.9546 -0.8657 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7254 3.9964 0.8992 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7392 2.1401 -1.5827 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0293 -2.3172 0.7664 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 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 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 20 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 2 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 1 0 37 40 1 0 37 41 1 0 34 42 1 0 42 43 2 0 42 44 1 0 44 45 1 0 31 46 1 0 26 47 1 0 19 48 1 0 11 49 1 0 10 50 1 0 5 51 1 0 4 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 57 59 1 0 59 60 1 0 56 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 66 68 1 0 68 69 1 0 65 70 1 0 64 71 1 0 63 72 1 0 55 73 1 0 54 74 1 0 3 75 1 0 7 2 1 0 14 9 1 0 21 16 1 0 27 19 1 0 31 26 1 0 35 30 1 0 39 34 1 0 58 53 1 0 67 62 1 0 1 76 1 0 1 77 1 0 1 78 1 0 2 79 1 0 3 80 1 0 4 81 1 0 5 82 1 0 6 83 1 0 9 84 1 0 10 85 1 0 11 86 1 0 12 87 1 0 12 88 1 0 14 89 1 0 16 90 1 0 17 91 1 0 17 92 1 0 18 93 1 0 18 94 1 0 20 95 1 0 22 96 1 0 22 97 1 0 22 98 1 0 23 99 1 0 23100 1 0 23101 1 0 24102 1 0 24103 1 0 25104 1 0 25105 1 0 27106 1 0 28107 1 0 28108 1 0 29109 1 0 32110 1 0 32111 1 0 33112 1 0 33113 1 0 35114 1 0 36115 1 0 36116 1 0 38117 1 0 38118 1 0 39119 1 0 39120 1 0 40121 1 0 40122 1 0 40123 1 0 41124 1 0 41125 1 0 41126 1 0 45127 1 0 45128 1 0 45129 1 0 46130 1 0 46131 1 0 46132 1 0 47133 1 0 47134 1 0 47135 1 0 48136 1 0 48137 1 0 48138 1 0 49139 1 0 50140 1 0 51141 1 0 53142 1 0 54143 1 0 55144 1 0 56145 1 0 57146 1 0 59147 1 0 59148 1 0 60149 1 0 62150 1 0 63151 1 0 64152 1 0 65153 1 0 66154 1 0 68155 1 0 68156 1 0 69157 1 0 70158 1 0 71159 1 0 72160 1 0 73161 1 0 74162 1 0 75163 1 0 M END

Standard InCHIKey	DFDNXBAKTBKOJE-OQYFAZLGSA-N
Standard InCHI	InChI=1S/C54H88O21/c1-24-33(58)42(74-45-39(64)37(62)41(29(22-56)71-45)73-44-38(63)36(61)35(60)28(21-55)70-44)40(65)46(69-24)75-43-34(59)27(57)23-68-47(43)72-32-13-14-51(6)30(50(32,4)5)12-15-53(8)31(51)11-10-25-26-20-49(2,3)16-18-54(26,48(66)67-9)19-17-52(25,53)7/h10,24,26-47,55-65H,11-23H2,1-9H3/t24-,26-,27-,28+,29+,30-,31+,32-,33-,34-,35+,36-,37+,38+,39+,40+,41+,42+,43+,44-,45-,46-,47-,51-,52+,53+,54-/m0/s1
SMILES	CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)OC)C)C)C)O)O)O)OC8C(C(C(C(O8)CO)OC9C(C(C(C(O9)CO)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1072.58	Volume:	1044.853 ? Van der Waals volume.
Dense:	1.027	LogP:	1.039 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.361 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.667 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	51.0
TPSA:	322.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	11.0	Rings:	9.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.075	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.718	Fsp³:	0.944
MCE-18:	193.333 ? 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:	0.1	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.114 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.349	Promiscuous compounds:	0.0

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.637	MDCK Permeability:	-5.039
Pgp-inhibitor:	0.0	Pgp-substrate:	0.9
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):	0.968
20% Bioavailability (F20%):	0.083	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014	MRP1:	1.0
Plasma Protein Binding (PPB):	55.172%	Volume Distribution (VD):	-0.461
Fu:	30.548% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.239	BCRP inhibitor:	0.0
BSEP inhibitor:	0.027

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.969	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.637	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
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):

-0.34

Half-life (T1/2):

3.479

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.23
Human Hepatotoxicity (H-HT):	0.388	Drug-induced Liver Injury (DILI):	0.214
AMES Toxicity:	0.317	Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.213	Skin Sensitization:	0.025
Carcinogencity:	0.01	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.367	Ototoxicity:	1.0
Hematotoxicity:	0.008	Drug-induced Nephrotoxicity:	0.015
Genotoxicity:	0.005	RPMI-8226 Immunitoxicity:	0.069
A549 Cytotoxicity:	0.037	Hek293 Cytotoxicity:	0.775
BCF:	1.322 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.509 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.564 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.044 ? 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
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[11575962]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	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

Activity Type	# Activity
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	7.8	ug.mL-1	PMID[8882431]

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 NPC475287 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	23338
0.1-0.2	22465
0.2-0.3	2684
0.3-0.4	731
0.4-0.5	378
0.5-0.6	86
0.6-0.7	79
0.7-0.8	0
0.8-0.85	5
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8807	High Similarity	NPC41061
0.8807	High Similarity	NPC227551
0.8649	High Similarity	NPC305981
0.8571	High Similarity	NPC261506
0.8571	High Similarity	NPC4328
0.8431	Intermediate Similarity	NPC475504
0.8208	Intermediate Similarity	NPC481078
0.8158	Intermediate Similarity	NPC236638
0.8158	Intermediate Similarity	NPC294453
0.8073	Intermediate Similarity	NPC79643
0.7931	Intermediate Similarity	NPC298034
0.7931	Intermediate Similarity	NPC71065
0.7928	Intermediate Similarity	NPC135904
0.7913	Intermediate Similarity	NPC43550
0.7881	Intermediate Similarity	NPC250247
0.7768	Intermediate Similarity	NPC123199
0.7719	Intermediate Similarity	NPC481080
0.7692	Intermediate Similarity	NPC112352
0.7658	Intermediate Similarity	NPC60557
0.7658	Intermediate Similarity	NPC67857
0.7542	Intermediate Similarity	NPC202828
0.7542	Intermediate Similarity	NPC119592
0.75	Intermediate Similarity	NPC220160
0.7456	Intermediate Similarity	NPC251263
0.735	Intermediate Similarity	NPC57484
0.7311	Intermediate Similarity	NPC65105
0.725	Intermediate Similarity	NPC481081
0.7167	Intermediate Similarity	NPC293330
0.7156	Intermediate Similarity	NPC63159
0.7143	Intermediate Similarity	NPC110633
0.7059	Intermediate Similarity	NPC476068
0.7043	Intermediate Similarity	NPC76972
0.7043	Intermediate Similarity	NPC469782
0.7043	Intermediate Similarity	NPC204414
0.6949	Remote Similarity	NPC475160
0.6949	Remote Similarity	NPC473714
0.6923	Remote Similarity	NPC133818
0.6881	Remote Similarity	NPC223301
0.6881	Remote Similarity	NPC171544
0.6829	Remote Similarity	NPC136768
0.6809	Remote Similarity	NPC469778
0.6763	Remote Similarity	NPC469776
0.6757	Remote Similarity	NPC46665
0.6754	Remote Similarity	NPC324875
0.6754	Remote Similarity	NPC292677
0.675	Remote Similarity	NPC488560
0.6738	Remote Similarity	NPC32723
0.6696	Remote Similarity	NPC295823
0.6696	Remote Similarity	NPC174720
0.6696	Remote Similarity	NPC475467
0.669	Remote Similarity	NPC481323
0.6667	Remote Similarity	NPC258617
0.6639	Remote Similarity	NPC165204
0.6637	Remote Similarity	NPC297263
0.6636	Remote Similarity	NPC469946
0.6613	Remote Similarity	NPC161717
0.6612	Remote Similarity	NPC54636
0.6607	Remote Similarity	NPC10607
0.6607	Remote Similarity	NPC480475
0.6606	Remote Similarity	NPC249848
0.6606	Remote Similarity	NPC107966
0.6599	Remote Similarity	NPC295941
0.6597	Remote Similarity	NPC135334
0.6587	Remote Similarity	NPC70809
0.6552	Remote Similarity	NPC481324
0.6518	Remote Similarity	NPC30735
0.6514	Remote Similarity	NPC475516
0.6496	Remote Similarity	NPC475486
0.6466	Remote Similarity	NPC481079
0.6446	Remote Similarity	NPC219180
0.6393	Remote Similarity	NPC100639
0.6379	Remote Similarity	NPC104372
0.6372	Remote Similarity	NPC160415
0.6364	Remote Similarity	NPC235405
0.632	Remote Similarity	NPC286457
0.6316	Remote Similarity	NPC164389
0.6296	Remote Similarity	NPC214484
0.6294	Remote Similarity	NPC469775
0.629	Remote Similarity	NPC85154
0.6284	Remote Similarity	NPC469777
0.6279	Remote Similarity	NPC224381
0.6276	Remote Similarity	NPC469774
0.6261	Remote Similarity	NPC475591
0.6261	Remote Similarity	NPC236870
0.6239	Remote Similarity	NPC276093
0.6218	Remote Similarity	NPC104137
0.6218	Remote Similarity	NPC26626
0.6218	Remote Similarity	NPC187290
0.6207	Remote Similarity	NPC222580
0.6186	Remote Similarity	NPC301449
0.6186	Remote Similarity	NPC601290
0.6182	Remote Similarity	NPC48499
0.6179	Remote Similarity	NPC155410
0.6174	Remote Similarity	NPC251768
0.6159	Remote Similarity	NPC469772
0.6149	Remote Similarity	NPC100925
0.6142	Remote Similarity	NPC475514
0.614	Remote Similarity	NPC192791
0.6134	Remote Similarity	NPC241909
0.6134	Remote Similarity	NPC80986
0.6129	Remote Similarity	NPC471550
0.6121	Remote Similarity	NPC235438
0.6102	Remote Similarity	NPC114484
0.6094	Remote Similarity	NPC471385
0.6083	Remote Similarity	NPC31838
0.6078	Remote Similarity	NPC469773
0.6053	Remote Similarity	NPC263756
0.6053	Remote Similarity	NPC213674
0.6034	Remote Similarity	NPC159309
0.6034	Remote Similarity	NPC86222
0.6016	Remote Similarity	NPC470876
0.6	Remote Similarity	NPC480473
0.6	Remote Similarity	NPC480474
0.5984	Remote Similarity	NPC21691
0.597	Remote Similarity	NPC480422
0.5932	Remote Similarity	NPC481082
0.5932	Remote Similarity	NPC164419
0.592	Remote Similarity	NPC166422
0.5896	Remote Similarity	NPC489209
0.5887	Remote Similarity	NPC123522
0.5887	Remote Similarity	NPC192600
0.5878	Remote Similarity	NPC302543
0.5877	Remote Similarity	NPC150400
0.5877	Remote Similarity	NPC127056
0.5873	Remote Similarity	NPC470218
0.5847	Remote Similarity	NPC148417
0.5833	Remote Similarity	NPC281148
0.5826	Remote Similarity	NPC39211
0.5814	Remote Similarity	NPC473452
0.5812	Remote Similarity	NPC104071
0.5812	Remote Similarity	NPC309714
0.5781	Remote Similarity	NPC4749
0.5763	Remote Similarity	NPC102439
0.5748	Remote Similarity	NPC283417
0.5748	Remote Similarity	NPC200049
0.5748	Remote Similarity	NPC191827
0.5714	Remote Similarity	NPC471384
0.5714	Remote Similarity	NPC90856
0.5704	Remote Similarity	NPC472268
0.5703	Remote Similarity	NPC47995
0.5691	Remote Similarity	NPC36831
0.5678	Remote Similarity	NPC117714
0.5678	Remote Similarity	NPC30289
0.5643	Remote Similarity	NPC489208
0.5641	Remote Similarity	NPC161674
0.5641	Remote Similarity	NPC80843
0.5634	Remote Similarity	NPC297950
0.563	Remote Similarity	NPC40775
0.563	Remote Similarity	NPC488526
0.563	Remote Similarity	NPC473459
0.563	Remote Similarity	NPC2370
0.5583	Remote Similarity	NPC68175
0.558	Remote Similarity	NPC33012
0.558	Remote Similarity	NPC477464
0.5573	Remote Similarity	NPC13998
0.5571	Remote Similarity	NPC475368
0.5556	Remote Similarity	NPC295371
0.5556	Remote Similarity	NPC157868
0.5526	Remote Similarity	NPC1046
0.552	Remote Similarity	NPC75287
0.5517	Remote Similarity	NPC56713
0.5508	Remote Similarity	NPC76497
0.5507	Remote Similarity	NPC8524
0.5492	Remote Similarity	NPC486563
0.5484	Remote Similarity	NPC187618
0.5474	Remote Similarity	NPC102505
0.5474	Remote Similarity	NPC488514
0.5469	Remote Similarity	NPC323341
0.5433	Remote Similarity	NPC268184
0.543	Remote Similarity	NPC472269
0.5426	Remote Similarity	NPC475209
0.5417	Remote Similarity	NPC114304
0.5413	Remote Similarity	NPC237503
0.5403	Remote Similarity	NPC486564
0.5397	Remote Similarity	NPC815
0.5385	Remote Similarity	NPC59804
0.5372	Remote Similarity	NPC180550
0.5372	Remote Similarity	NPC35405
0.537	Remote Similarity	NPC167383
0.5362	Remote Similarity	NPC293031
0.536	Remote Similarity	NPC488564
0.5349	Remote Similarity	NPC470911
0.5339	Remote Similarity	NPC58448
0.5339	Remote Similarity	NPC473373
0.5312	Remote Similarity	NPC610204
0.531	Remote Similarity	NPC128925
0.5308	Remote Similarity	NPC480419
0.5299	Remote Similarity	NPC203354
0.5294	Remote Similarity	NPC309223
0.5294	Remote Similarity	NPC37860
0.5285	Remote Similarity	NPC275668
0.5285	Remote Similarity	NPC257468
0.5285	Remote Similarity	NPC609763
0.5263	Remote Similarity	NPC484061
0.5263	Remote Similarity	NPC484062
0.5259	Remote Similarity	NPC29069
0.5252	Remote Similarity	NPC68767
0.5246	Remote Similarity	NPC44716
0.5246	Remote Similarity	NPC173859

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475287 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7481
0.1-0.2	1607
0.2-0.3	54
0.3-0.4	8
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