NPASS Compound

Natural Product: NPC242611

Natural Product ID	NPC242611
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-[(Alpha-L-Arabinopyranosyl)Oxy]-16Alpha-Hydroxyolean-12-En-28-Oic Acid
IUPAC Name	(4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL538942
PubChem CID	15379012
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 99104 0 0 0 0 0 0 0 0999 V2000 -5.5219 2.8764 1.6116 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5628 2.4957 0.1480 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8728 3.8286 -0.5751 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7702 1.6329 -0.0736 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4649 0.3030 0.5713 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4371 -0.3783 -0.3016 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3291 0.5101 -0.8014 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2716 1.9045 -0.3532 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1110 -0.3215 -0.6448 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4461 -0.6742 -1.7083 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2128 -1.5133 -1.6495 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4741 -0.9988 -0.4663 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0024 -1.2312 -0.4754 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4632 -2.6139 -0.5522 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5545 -0.5412 -1.7432 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0534 -0.8150 -1.7886 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7824 -0.1506 -0.6620 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0259 -0.0858 0.6300 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7492 -0.9497 1.6396 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2030 1.3315 1.2446 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5940 -0.3600 0.6030 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9886 -0.8648 1.8912 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4793 -0.5034 1.8503 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2482 -1.2822 0.7645 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2609 -2.6909 1.2581 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6656 -0.8007 0.6677 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8988 0.1302 1.8236 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7364 -1.8879 0.9476 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0291 -1.6753 0.2671 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0644 -2.0475 1.1768 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0974 -0.5136 -0.5476 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0551 0.4069 -0.8920 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0872 0.6394 0.1693 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9655 1.7867 -0.3071 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6340 1.3810 -1.6328 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0443 0.0606 -2.0986 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7099 -0.0630 -2.0052 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9978 1.1513 -1.4480 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0010 2.0328 0.5882 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5919 0.8693 1.4404 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3162 -0.7447 -1.5068 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0446 -0.3003 -2.6466 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4127 -1.5692 -1.3324 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1393 2.2494 2.2639 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4323 2.8519 1.8967 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8440 3.9312 1.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8966 4.1252 -0.2893 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1812 4.5621 -0.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6829 3.7613 -1.6449 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6360 2.1391 0.3949 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9520 1.4249 -1.1495 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4253 -0.2826 0.4875 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1788 0.3627 1.6228 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5167 0.6041 -1.9254 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4830 2.1751 0.3805 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9678 2.6026 -1.2091 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7699 -0.3630 -2.7290 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7048 -1.5208 -2.6061 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4929 -2.6040 -1.4916 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5223 0.1387 -0.5595 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4277 -2.9357 -1.6401 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4989 -2.7006 -0.1619 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8916 -3.3965 -0.0359 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1945 -0.9775 -2.6684 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3928 0.5444 -1.7012 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1683 -1.8893 -1.8882 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3711 -0.3939 -2.7924 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8554 0.9245 -1.0239 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2216 -1.8666 1.9285 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9418 -0.4195 2.6173 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7668 -1.1395 1.2409 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2021 1.2841 2.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2991 1.8922 0.9456 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1044 1.8187 0.8152 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0675 0.6369 0.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2325 -1.9085 1.9759 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3867 -0.3153 2.7771 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4290 0.5600 1.4635 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8609 -0.6234 2.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0621 -2.7613 2.0529 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3740 -2.9629 1.9075 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4663 -3.4707 0.5328 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8090 -0.5550 2.7308 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2347 0.9457 1.9874 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9269 0.4948 1.9421 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3742 -2.8955 0.6007 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9066 -2.0135 2.0364 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1649 -2.4780 -0.5370 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0423 -3.0504 1.2785 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5844 1.3770 -1.2356 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7436 -0.2490 0.2631 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4236 2.7232 -0.4682 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5502 2.1807 -2.3958 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5437 -0.7608 -1.5138 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3993 -0.0926 -3.1462 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3439 0.8380 -2.3172 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6965 1.3170 0.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1014 0.4062 2.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9027 -2.0093 -2.0959 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 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 1 1 26 28 1 0 28 29 1 0 29 30 1 0 17 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 35 38 1 0 34 39 1 0 33 40 1 0 6 41 1 6 41 42 2 0 41 43 1 0 8 2 1 0 26 9 1 0 37 32 1 0 29 6 1 0 24 12 1 0 21 13 1 0 1 44 1 0 1 45 1 0 1 46 1 0 3 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 7 54 1 6 8 55 1 0 8 56 1 0 10 57 1 0 11 58 1 0 11 59 1 0 12 60 1 6 14 61 1 0 14 62 1 0 14 63 1 0 15 64 1 0 15 65 1 0 16 66 1 0 16 67 1 0 17 68 1 6 19 69 1 0 19 70 1 0 19 71 1 0 20 72 1 0 20 73 1 0 20 74 1 0 21 75 1 6 22 76 1 0 22 77 1 0 23 78 1 0 23 79 1 0 25 80 1 0 25 81 1 0 25 82 1 0 27 83 1 0 27 84 1 0 27 85 1 0 28 86 1 0 28 87 1 0 29 88 1 6 30 89 1 0 32 90 1 6 33 91 1 1 34 92 1 6 35 93 1 6 36 94 1 0 36 95 1 0 38 96 1 0 39 97 1 0 40 98 1 0 43 99 1 0 M END

Standard InCHIKey	SZXCDOOFLYYOCZ-HDYQOPGWSA-N
Standard InCHI	InChI=1S/C35H56O8/c1-30(2)14-15-35(29(40)41)20(16-30)19-8-9-23-32(5)12-11-25(43-28-27(39)26(38)21(36)18-42-28)31(3,4)22(32)10-13-33(23,6)34(19,7)17-24(35)37/h8,20-28,36-39H,9-18H2,1-7H3,(H,40,41)/t20-,21-,22-,23+,24+,25-,26-,27+,28-,32-,33+,34+,35+/m0/s1
SMILES	CC1(C)CC[C@]2([C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	604.4	Volume:	627.626 ? Van der Waals volume.
Dense:	0.963	LogP:	3.063 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.363 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.962 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	33.0
TPSA:	136.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.232	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.297	Fsp³:	0.914
MCE-18:	129.075 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.921	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:	0.185	Promiscuous compounds:	0.09

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.732	MDCK Permeability:	-5.162
Pgp-inhibitor:	0.007	Pgp-substrate:	0.007
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):	0.005
20% Bioavailability (F20%):	0.376	30% Bioavailability (F30%):	0.274
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083	MRP1:	0.782
Plasma Protein Binding (PPB):	84.376%	Volume Distribution (VD):	-0.51
Fu:	11.197% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.981	BCRP inhibitor:	0.019
BSEP inhibitor:	0.275

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.009
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.985
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.034
HLM stability:	0.011 ? 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):

0.639

Half-life (T1/2):

1.61

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.025
Human Hepatotoxicity (H-HT):	0.786	Drug-induced Liver Injury (DILI):	0.855
AMES Toxicity:	0.699	Rat Oral Acute Toxicity:	0.197
Maximum Recommended Daily Dose:	0.129	Skin Sensitization:	0.999
Carcinogencity:	0.869	Eye Corrosion:	0.002
Eye Irritation:	0.286	Respiratory Toxicity:	0.76
Drug-induced Neurotoxicity:	0.028	Ototoxicity:	0.822
Hematotoxicity:	0.759	Drug-induced Nephrotoxicity:	0.98
Genotoxicity:	0.741	RPMI-8226 Immunitoxicity:	0.063
A549 Cytotoxicity:	0.669	Hek293 Cytotoxicity:	0.315
BCF:	1.467 ? 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:	3.954 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.432 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.741 ? 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
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843584]
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	antarctic	n.a.	PMID[15270575]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	Eukaryota	underground parts	n.a.	n.a.	PMID[19449879]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407007]
NPO26453	Prunus lusitanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37240175]
NPO25793	Gremmeniella abietina	Species	Helotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3346	Piper sanctum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26109	Pilocarpus spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25926	Tephrosia pumila	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26903	Plectranthus purpuratus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26213	Tephrosia vogelii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26625	Stichopus chloronotus	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24378	Osmanthus heterophyllus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26078	Mussaenda parviflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26352	Heuchera cylindrica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18292	Guarea trichilioides	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26952	Cineraria geifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2344	Carlina acanthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2039	Callerya cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26135	Walsura tubulata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26078	Mussaenda parviflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26952	Cineraria geifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26289	Lecidella chodati	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24378	Osmanthus heterophyllus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11845	Petrorhagia dubia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25873	Thaminophyllum multiflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13781	Eremostachys moluccelloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26026	Vitis silvestris	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26563	Alectoria japonica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26453	Prunus lusitanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18292	Guarea trichilioides	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26535	Balanus glandula	Species	Balanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26352	Heuchera cylindrica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26625	Stichopus chloronotus	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26754	Stevia connata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25952	Lastrea thelypteris	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26213	Tephrosia vogelii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2344	Carlina acanthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26430	Aplysina laevis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25741	Aster ageratoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26884	Helichrysum davenportii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27377	Diaporthe helianthi	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25793	Gremmeniella abietina	Species	Helotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26053	Pluchea suaveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26109	Pilocarpus spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26980	Halocarpus biformis	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26903	Plectranthus purpuratus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2039	Callerya cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7214	Bufotes viridis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26186	Stereocaulon leprocauloides	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26377	Amelanchier vulgaris	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26678	Calea pilosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25849	Streptomyces lomondensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3346	Piper sanctum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26408	Melanophryniscus moreirae	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26727	Eremocarpus setiger	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25926	Tephrosia pumila	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19823	Vicia benghalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25997	Senecio rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO137	Nepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26244	Panax papyrifer	Species	Araliaceae	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	=	5.6	ug.mL-1	PMID[19449879]

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 NPC242611 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	19538
0.1-0.2	25252
0.2-0.3	3647
0.3-0.4	976
0.4-0.5	320
0.5-0.6	68
0.6-0.7	32
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8588	High Similarity	NPC488516
0.8148	Intermediate Similarity	NPC31839
0.8132	Intermediate Similarity	NPC488515
0.8125	Intermediate Similarity	NPC283849
0.7667	Intermediate Similarity	NPC80843
0.7579	Intermediate Similarity	NPC75318
0.7449	Intermediate Similarity	NPC288205
0.7449	Intermediate Similarity	NPC51465
0.7444	Intermediate Similarity	NPC480424
0.7262	Intermediate Similarity	NPC28198
0.7262	Intermediate Similarity	NPC476123
0.7037	Intermediate Similarity	NPC601365
0.7011	Intermediate Similarity	NPC100383
0.6989	Remote Similarity	NPC6377
0.6989	Remote Similarity	NPC488561
0.6989	Remote Similarity	NPC208381
0.69	Remote Similarity	NPC475486
0.6768	Remote Similarity	NPC37134
0.6701	Remote Similarity	NPC104400
0.6701	Remote Similarity	NPC10320
0.6667	Remote Similarity	NPC469945
0.6667	Remote Similarity	NPC606107
0.663	Remote Similarity	NPC76999
0.6535	Remote Similarity	NPC291903
0.65	Remote Similarity	NPC79718
0.65	Remote Similarity	NPC228784
0.65	Remote Similarity	NPC324341
0.65	Remote Similarity	NPC601810
0.6442	Remote Similarity	NPC475119
0.6436	Remote Similarity	NPC145899
0.64	Remote Similarity	NPC481082
0.64	Remote Similarity	NPC164419
0.6381	Remote Similarity	NPC473824
0.6354	Remote Similarity	NPC127056
0.6333	Remote Similarity	NPC286347
0.625	Remote Similarity	NPC56713
0.6238	Remote Similarity	NPC73829
0.6226	Remote Similarity	NPC200788
0.6111	Remote Similarity	NPC243680
0.6071	Remote Similarity	NPC222047
0.6044	Remote Similarity	NPC177246
0.6038	Remote Similarity	NPC280941
0.6038	Remote Similarity	NPC235772
0.6	Remote Similarity	NPC204407
0.6	Remote Similarity	NPC480938
0.5938	Remote Similarity	NPC164194
0.5909	Remote Similarity	NPC166422
0.5849	Remote Similarity	NPC488209
0.5833	Remote Similarity	NPC201657
0.5816	Remote Similarity	NPC136877
0.58	Remote Similarity	NPC472949
0.5773	Remote Similarity	NPC127853
0.5773	Remote Similarity	NPC1046
0.5758	Remote Similarity	NPC25605
0.5758	Remote Similarity	NPC59804
0.5755	Remote Similarity	NPC324875
0.5755	Remote Similarity	NPC292677
0.5743	Remote Similarity	NPC22956
0.5728	Remote Similarity	NPC180550
0.5728	Remote Similarity	NPC35405
0.5714	Remote Similarity	NPC484832
0.5714	Remote Similarity	NPC119794
0.57	Remote Similarity	NPC114441
0.57	Remote Similarity	NPC109079
0.5625	Remote Similarity	NPC284807
0.5619	Remote Similarity	NPC257468
0.56	Remote Similarity	NPC174679
0.56	Remote Similarity	NPC279554
0.5596	Remote Similarity	NPC11242
0.5581	Remote Similarity	NPC471588
0.5529	Remote Similarity	NPC120840
0.551	Remote Similarity	NPC475472
0.5487	Remote Similarity	NPC219180
0.5481	Remote Similarity	NPC114304
0.5464	Remote Similarity	NPC294112
0.5455	Remote Similarity	NPC270667
0.5455	Remote Similarity	NPC62725
0.5413	Remote Similarity	NPC488564
0.5408	Remote Similarity	NPC191410
0.5398	Remote Similarity	NPC323341
0.5361	Remote Similarity	NPC128925
0.5354	Remote Similarity	NPC90856
0.5351	Remote Similarity	NPC251263
0.5341	Remote Similarity	NPC488521
0.5333	Remote Similarity	NPC117714
0.5333	Remote Similarity	NPC30289
0.5323	Remote Similarity	NPC120667
0.5323	Remote Similarity	NPC278272
0.5321	Remote Similarity	NPC301449
0.5321	Remote Similarity	NPC601290
0.5304	Remote Similarity	NPC475140
0.5283	Remote Similarity	NPC488526
0.5281	Remote Similarity	NPC6255
0.5273	Remote Similarity	NPC477193
0.5229	Remote Similarity	NPC276093
0.5225	Remote Similarity	NPC187290
0.5214	Remote Similarity	NPC4749
0.52	Remote Similarity	NPC204458
0.5196	Remote Similarity	NPC12288
0.5179	Remote Similarity	NPC480939
0.5172	Remote Similarity	NPC283417
0.5172	Remote Similarity	NPC200049
0.5149	Remote Similarity	NPC78046
0.5143	Remote Similarity	NPC263756
0.5143	Remote Similarity	NPC213674
0.5143	Remote Similarity	NPC469946
0.513	Remote Similarity	NPC471384
0.5093	Remote Similarity	NPC139044
0.5089	Remote Similarity	NPC104137
0.5089	Remote Similarity	NPC26626
0.505	Remote Similarity	NPC473481
0.5041	Remote Similarity	NPC471385
0.5041	Remote Similarity	NPC161717

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC242611 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6137
0.1-0.2	2940
0.2-0.3	64
0.3-0.4	8
0.4-0.5	0
0.5-0.6	1
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
0.5446	Remote Similarity	NPD8295	Clinical (unspecified phase)

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