NPASS Compound

Natural Product: NPC20281

Natural Product ID	NPC20281
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GYHJUCGZRYCVFH-ZRKNEZIWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 81 86 0 0 0 0 0 0 0 0999 V2000 -7.2965 2.7068 0.5192 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0981 2.1662 -0.2161 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4696 1.3697 -1.4295 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6356 -0.0898 -1.0981 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3616 -0.6581 -0.4891 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4672 0.5000 -0.0089 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2078 1.4994 0.5545 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5772 0.0276 0.9105 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2521 0.0980 0.5562 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5553 1.0711 1.4783 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1790 1.2653 0.8773 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5559 -0.0316 1.2338 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5929 -0.0841 2.7471 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1011 -1.2270 0.6225 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5934 -1.5408 -0.7133 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9868 -2.0718 -0.4836 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5480 -1.3556 0.7440 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9847 0.0200 0.7465 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8337 1.0000 1.5158 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1556 1.0707 0.7808 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8358 -0.2398 0.5729 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0346 -0.2412 1.5547 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4547 -0.4174 -0.7595 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3129 -1.7040 -1.1168 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6164 -2.4784 -0.0941 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0422 -1.4482 0.8389 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3677 -1.9115 2.1442 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1227 0.5535 -1.6034 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3354 1.8227 -1.3764 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0515 2.4615 -2.4919 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4098 3.6665 -2.5909 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2513 1.4614 -3.4136 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7171 0.2544 -2.9531 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5585 -1.2177 0.4469 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -0.8691 -2.1442 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2151 -1.5398 -2.0134 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6454 1.9106 -1.9498 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1573 3.7500 0.8632 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2142 2.7124 -0.1043 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5022 2.0331 1.3756 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5516 3.0885 -0.5926 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6912 1.5485 -2.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4040 -0.1586 -0.3040 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8560 -1.2163 -1.3019 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5565 -1.3838 0.3227 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0006 0.8823 -0.9579 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2197 0.5744 -0.4490 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0901 2.0397 1.3781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5223 0.7052 2.5153 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3426 2.1088 1.3295 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2560 1.3206 -0.2207 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2299 -0.7323 3.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5752 0.9420 3.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5214 -0.5552 3.1416 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1800 -2.1033 1.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0050 -2.3563 -1.1695 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5432 -0.6897 -1.4076 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9000 -3.1728 -0.2930 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6120 -1.8882 -1.3638 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1418 -1.9768 1.6025 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9436 0.4087 -0.3135 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3657 1.9996 1.3999 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9396 0.8011 2.5777 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9162 1.5118 -0.2083 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7702 1.7988 1.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7844 -0.9992 1.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6863 -0.5784 2.5590 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4460 0.7676 1.6933 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6606 -2.1533 -2.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4092 -3.0982 0.4222 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8920 -3.2065 -0.4908 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9189 -2.7442 2.3580 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0521 2.3788 -0.4974 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5477 -0.4704 -2.8254 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9362 -0.1108 -3.6528 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0539 -1.8926 1.2110 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8543 -1.6821 -0.5193 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3520 -2.1161 -2.9773 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2073 -2.3365 -1.2244 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1194 -0.9025 -1.9407 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3918 1.3529 -1.6107 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 1 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 1 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 4 35 1 0 35 36 1 0 3 37 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 38 1 0 1 39 1 0 1 40 1 0 2 41 1 6 3 42 1 6 4 43 1 1 5 44 1 0 5 45 1 0 6 46 1 6 9 47 1 6 10 48 1 0 10 49 1 0 11 50 1 0 11 51 1 0 13 52 1 0 13 53 1 0 13 54 1 0 14 55 1 1 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 1 18 61 1 6 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 22 66 1 0 22 67 1 0 22 68 1 0 24 69 1 0 25 70 1 0 25 71 1 0 27 72 1 0 29 73 1 0 33 74 1 0 33 75 1 0 34 76 1 0 34 77 1 0 36 78 1 0 36 79 1 0 36 80 1 0 37 81 1 0 M END

Standard InCHIKey	GYHJUCGZRYCVFH-ZRKNEZIWSA-N
Standard InCHI	InChI=1S/C30H44O7/c1-17-27(32)24(34-4)15-26(36-17)37-20-7-10-28(2)19(14-20)5-6-23-22(28)8-11-29(3)21(9-12-30(23,29)33)18-13-25(31)35-16-18/h9,13,17,19-20,22-24,26-27,32-33H,5-8,10-12,14-16H2,1-4H3/t17-,19-,20+,22+,23-,24+,26+,27+,28+,29-,30+/m1/s1
SMILES	C[C@@H]1[C@@H]([C@H](C[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)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	516.31	Volume:	529.719 ? Van der Waals volume.
Dense:	0.975	LogP:	2.832 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.075 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.599 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	32.0
TPSA:	94.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.43	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.232	Fsp³:	0.833
MCE-18:	105.018 ? 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:	0.778	Fluc inhibitor:	0.049 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.046 ? 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:	0.179	Promiscuous compounds:	0.42

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.427	MDCK Permeability:	-5.089
Pgp-inhibitor:	0.717	Pgp-substrate:	0.232
PAMPA:	0.777 ? 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):	0.023
20% Bioavailability (F20%):	0.236	30% Bioavailability (F30%):	0.246
50% Bioavailability (F50%):	0.701

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147	MRP1:	0.905
Plasma Protein Binding (PPB):	89.332%	Volume Distribution (VD):	0.273
Fu:	10.673% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.928
OATP1B3 inhibitor:	0.775	BCRP inhibitor:	0.063
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.946	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.733	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.975	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.56
HLM stability:	0.136 ? 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):

7.559

Half-life (T1/2):

2.017

ADMET: Toxicity

hERG Blockers:	0.063	hERG Blockers (10um):	0.352
Human Hepatotoxicity (H-HT):	0.789	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.988	Rat Oral Acute Toxicity:	0.907
Maximum Recommended Daily Dose:	0.944	Skin Sensitization:	1.0
Carcinogencity:	0.975	Eye Corrosion:	0.0
Eye Irritation:	0.041	Respiratory Toxicity:	0.735
Drug-induced Neurotoxicity:	0.222	Ototoxicity:	0.778
Hematotoxicity:	0.933	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.975	RPMI-8226 Immunitoxicity:	0.491
A549 Cytotoxicity:	0.967	Hek293 Cytotoxicity:	0.867
BCF:	0.666 ? 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:	3.44 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.172 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.444 ? 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 NPC20281 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	17046
0.1-0.2	28440
0.2-0.3	3984
0.3-0.4	252
0.4-0.5	89
0.5-0.6	31
0.6-0.7	10
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
0.7195	Intermediate Similarity	NPC99080
0.7108	Intermediate Similarity	NPC84949
0.7108	Intermediate Similarity	NPC480562
0.7108	Intermediate Similarity	NPC74945
0.7108	Intermediate Similarity	NPC31354
0.7108	Intermediate Similarity	NPC69576
0.6966	Remote Similarity	NPC488941
0.6966	Remote Similarity	NPC488940
0.6739	Remote Similarity	NPC488939
0.6705	Remote Similarity	NPC103534
0.6705	Remote Similarity	NPC44899
0.6705	Remote Similarity	NPC304260
0.6705	Remote Similarity	NPC29639
0.618	Remote Similarity	NPC483822
0.6111	Remote Similarity	NPC268326
0.6111	Remote Similarity	NPC153085
0.5843	Remote Similarity	NPC477580
0.5652	Remote Similarity	NPC484202
0.5495	Remote Similarity	NPC479356
0.5495	Remote Similarity	NPC479355
0.5484	Remote Similarity	NPC93883
0.5444	Remote Similarity	NPC471633
0.5435	Remote Similarity	NPC199428
0.5435	Remote Similarity	NPC109448
0.5435	Remote Similarity	NPC152615
0.5435	Remote Similarity	NPC310341
0.5376	Remote Similarity	NPC290693
0.5354	Remote Similarity	NPC55532
0.5326	Remote Similarity	NPC34390
0.5312	Remote Similarity	NPC488935
0.5312	Remote Similarity	NPC488936
0.5263	Remote Similarity	NPC193893
0.5253	Remote Similarity	NPC231518
0.5253	Remote Similarity	NPC488944
0.5217	Remote Similarity	NPC481208
0.5213	Remote Similarity	NPC180079
0.5208	Remote Similarity	NPC72260
0.52	Remote Similarity	NPC486143
0.52	Remote Similarity	NPC486142
0.52	Remote Similarity	NPC486149
0.5161	Remote Similarity	NPC5311
0.5155	Remote Similarity	NPC5883
0.5109	Remote Similarity	NPC99620
0.5094	Remote Similarity	NPC120390
0.5094	Remote Similarity	NPC475419
0.5051	Remote Similarity	NPC115349
0.5046	Remote Similarity	NPC474423

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC20281 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6567
0.1-0.2	2485
0.2-0.3	84
0.3-0.4	4
0.4-0.5	3
0.5-0.6	5
0.6-0.7	1
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
0.6	Remote Similarity	NPD8377	Phase 4
0.5773	Remote Similarity	NPD8378	Pre-clinical
0.5773	Remote Similarity	NPD8379	Approved
0.5253	Remote Similarity	NPD8033	Approved
0.5213	Remote Similarity	NPD8335	Phase 4
0.5208	Remote Similarity	NPD8294	Phase 4

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