NPASS Compound

Natural Product: NPC110041

Natural Product ID	NPC110041
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RICACBKPZFLFFK-VFBKJSQWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10816404
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 85 90 0 0 0 0 0 0 0 0999 V2000 -5.8217 -2.4541 -0.8578 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3484 -1.6424 0.3315 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2852 -0.5584 -0.1041 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6998 0.7863 0.3409 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2564 0.7802 -0.1540 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5187 -0.2575 0.6277 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3438 -1.2295 1.1699 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4694 -0.7812 -0.0998 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2224 -0.5197 0.4477 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5799 -1.8552 0.7497 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1173 -1.7641 0.9948 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6365 -0.9698 -0.0374 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4050 -1.6546 -1.3785 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0332 0.4161 -0.1484 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1959 1.2230 1.1095 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5116 1.0427 1.7875 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4816 0.4689 0.7528 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0758 -0.9234 0.3504 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9768 -1.3237 -0.7986 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4188 -1.1497 -0.5084 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8125 0.1938 0.0321 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8917 1.2526 -1.0263 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0864 0.0119 0.7566 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8162 -0.2577 2.0504 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3456 -0.2742 2.2729 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8901 0.6122 1.1717 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1258 1.9311 1.5316 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4473 0.0682 0.2676 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5652 -0.1242 0.9631 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7332 0.0079 0.1390 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9342 -0.1234 0.5442 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2765 0.2960 -1.1315 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8487 0.3772 -1.1191 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4319 0.3195 -0.4919 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6936 2.0347 -0.1051 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3978 2.4755 -1.4054 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3681 1.7929 -0.3415 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9440 2.6885 0.5760 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3135 -0.5130 -1.5111 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5309 -3.4665 -0.5003 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6969 -2.5937 -1.5393 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0314 -1.9342 -1.4009 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9660 -2.3807 0.9179 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3229 -0.6888 0.2566 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7750 0.9217 1.4240 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3288 0.4409 -1.2289 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0518 0.2681 1.5130 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3893 0.0728 1.3774 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0559 -2.2076 1.7109 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8779 -2.6127 -0.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0605 -1.4068 2.0315 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2988 -2.8017 0.9642 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6949 -1.0235 -2.2312 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7130 -1.7925 -1.4648 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8206 -2.6770 -1.4058 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5074 0.9403 -1.0304 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6075 0.9699 1.8312 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0371 2.2961 0.8441 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4816 0.4556 2.7060 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9368 2.0427 2.0597 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3364 1.1123 -0.1488 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2912 -1.6656 1.1709 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6660 -0.8264 -1.7390 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7942 -2.4143 -0.9645 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7931 -1.9512 0.1794 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9830 -1.2981 -1.4561 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3912 0.8178 -1.9140 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8816 1.5588 -1.3857 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4880 2.1044 -0.6770 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5365 -0.4395 2.8332 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0757 0.1198 3.2744 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0317 -1.3350 2.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9371 1.9997 2.1135 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6043 -0.3563 2.0365 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6147 1.4232 -1.4250 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4932 -0.3704 -1.8352 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8329 1.3726 -0.4098 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5653 0.0575 -1.5658 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6904 1.7762 -1.8739 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9893 3.5065 -1.3840 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3383 2.4601 -2.0146 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1379 3.1168 1.1824 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6501 2.0788 1.1810 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4543 3.4986 0.0182 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4463 0.4281 -1.7894 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 6 12 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 6 21 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 1 23 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 14 34 1 0 5 35 1 0 35 36 1 0 4 37 1 0 37 38 1 0 3 39 1 0 7 2 1 0 34 9 1 0 18 12 1 0 26 21 1 0 33 28 1 0 26 17 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 1 3 44 1 1 4 45 1 1 5 46 1 6 6 47 1 1 9 48 1 1 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 13 53 1 0 13 54 1 0 13 55 1 0 14 56 1 6 15 57 1 0 15 58 1 0 16 59 1 0 16 60 1 0 17 61 1 6 18 62 1 1 19 63 1 0 19 64 1 0 20 65 1 0 20 66 1 0 22 67 1 0 22 68 1 0 22 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 27 73 1 0 29 74 1 0 33 75 1 0 33 76 1 0 34 77 1 0 34 78 1 0 36 79 1 0 36 80 1 0 36 81 1 0 38 82 1 0 38 83 1 0 38 84 1 0 39 85 1 0 M END

Standard InCHIKey	RICACBKPZFLFFK-VFBKJSQWSA-N
Standard InCHI	InChI=1S/C31H46O8/c1-17-25(33)26(35-4)27(36-5)28(38-17)39-20-8-11-29(2)19(15-20)6-7-23-22(29)9-12-30(3)21(10-13-31(23,30)34)18-14-24(32)37-16-18/h10,14,17,19-20,22-23,25-28,33-34H,6-9,11-13,15-16H2,1-5H3/t17-,19-,20+,22+,23-,25+,26+,27-,28+,29+,30-,31+/m1/s1
SMILES	C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)C(=CC[C@]32O)C2=CC(=O)OC2)C1)OC)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	546.32	Volume:	555.806 ? Van der Waals volume.
Dense:	0.983	LogP:	2.365 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.891 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.236 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	32.0
TPSA:	103.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.398	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.311	Fsp³:	0.839
MCE-18:	106.737 ? 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:	0.798	Fluc inhibitor:	0.042 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.039 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.163	Promiscuous compounds:	0.353

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.337	MDCK Permeability:	-5.09
Pgp-inhibitor:	0.933	Pgp-substrate:	0.24
PAMPA:	0.75 ? 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):	0.043
20% Bioavailability (F20%):	0.364	30% Bioavailability (F30%):	0.268
50% Bioavailability (F50%):	0.823

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043	MRP1:	0.967
Plasma Protein Binding (PPB):	95.074%	Volume Distribution (VD):	0.317
Fu:	3.388% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.985
OATP1B3 inhibitor:	0.873	BCRP inhibitor:	0.026
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.941	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.041	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.204	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.005
HLM stability:	0.097 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.893

Half-life (T1/2):

2.018

ADMET: Toxicity

hERG Blockers:	0.047	hERG Blockers (10um):	0.202
Human Hepatotoxicity (H-HT):	0.773	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.98	Rat Oral Acute Toxicity:	0.726
Maximum Recommended Daily Dose:	0.692	Skin Sensitization:	1.0
Carcinogencity:	0.924	Eye Corrosion:	0.0
Eye Irritation:	0.045	Respiratory Toxicity:	0.652
Drug-induced Neurotoxicity:	0.068	Ototoxicity:	0.814
Hematotoxicity:	0.97	Drug-induced Nephrotoxicity:	0.993
Genotoxicity:	0.963	RPMI-8226 Immunitoxicity:	0.511
A549 Cytotoxicity:	0.952	Hek293 Cytotoxicity:	0.858
BCF:	0.636 ? 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:	3.446 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.087 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.391 ? 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
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1038/ncomms4886]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11277760]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19731587]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37726667]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39382805]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO1607	Croton rhamnifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2361	Aconitum brevicalcaratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3146	Ammodendron conollyi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO351	Cirsium dipsacolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6377	Cocculus diversifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8585	Verpa digitaliformis	Species	Morchellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1308	Veronica pectinata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15583	Tripodanthus acutifolius	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6776	Trifolium apertum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO715	Teucrium pestalozzae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5197	Streptomyces eurythermus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6974	Solanum racemigerum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20132	Scutellaria seleriana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7097	Rhynchosporium orthosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8840	Ptilidium ciliare	Species	Ptilidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4253	Viguiera annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4082	Ophiarthrum elegans	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8472	Knightia deplanchei	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5591	Fucus spiralis	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5980	Eria subsessilis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5591	Fucus spiralis	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20132	Scutellaria seleriana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO715	Teucrium pestalozzae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8472	Knightia deplanchei	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15583	Tripodanthus acutifolius	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8840	Ptilidium ciliare	Species	Ptilidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4082	Ophiarthrum elegans	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2361	Aconitum brevicalcaratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6776	Trifolium apertum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5197	Streptomyces eurythermus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO351	Cirsium dipsacolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8585	Verpa digitaliformis	Species	Morchellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6377	Cocculus diversifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7097	Rhynchosporium orthosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6974	Solanum racemigerum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1607	Croton rhamnifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5980	Eria subsessilis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3146	Ammodendron conollyi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4253	Viguiera annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1308	Veronica pectinata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10021	Nerium oleander	Species	Apocynaceae	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 NPC110041 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	16749
0.1-0.2	28584
0.2-0.3	4148
0.3-0.4	260
0.4-0.5	85
0.5-0.6	23
0.6-0.7	5
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
0.7191	Intermediate Similarity	NPC488939
0.6824	Remote Similarity	NPC93883
0.6667	Remote Similarity	NPC488941
0.6667	Remote Similarity	NPC488940
0.6591	Remote Similarity	NPC488935
0.6591	Remote Similarity	NPC488936
0.5556	Remote Similarity	NPC479356
0.5556	Remote Similarity	NPC479355
0.5556	Remote Similarity	NPC99080
0.5495	Remote Similarity	NPC199428
0.5495	Remote Similarity	NPC84949
0.5495	Remote Similarity	NPC109448
0.5495	Remote Similarity	NPC480562
0.5495	Remote Similarity	NPC74945
0.5495	Remote Similarity	NPC310341
0.5495	Remote Similarity	NPC31354
0.5495	Remote Similarity	NPC69576
0.5385	Remote Similarity	NPC6108
0.5385	Remote Similarity	NPC89514
0.53	Remote Similarity	NPC486146
0.5208	Remote Similarity	NPC103534
0.5208	Remote Similarity	NPC44899
0.5208	Remote Similarity	NPC5883
0.5208	Remote Similarity	NPC304260
0.5208	Remote Similarity	NPC29639
0.5146	Remote Similarity	NPC488938
0.5146	Remote Similarity	NPC488937
0.51	Remote Similarity	NPC55532
0.5054	Remote Similarity	NPC5311

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC110041 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6534
0.1-0.2	2531
0.2-0.3	68
0.3-0.4	8
0.4-0.5	8
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