NPASS Compound

Natural Product: NPC150531

Natural Product ID	NPC150531
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ecdysone
IUPAC Name	(2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms	Ecdysone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL549300
PubChem CID	19212
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0002198] Pentahydroxy bile acids, alcohols and derivatives

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 77 80 0 0 0 0 0 0 0 0999 V2000 2.1714 -0.0288 2.3631 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3903 -0.8223 1.0437 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5095 -0.3106 -0.0138 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6208 -1.0616 -1.3148 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1678 -1.4111 -1.7444 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5493 -0.2555 -1.1130 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9939 -0.3952 -0.9837 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7131 -1.3776 -1.4631 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1562 -1.3917 -1.2608 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8600 -2.3105 -1.7647 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8496 -0.3436 -0.4664 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5726 0.6733 -1.2753 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6037 1.3569 -0.3679 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0496 1.4130 1.0184 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5584 1.4827 1.1032 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8628 0.2772 0.4948 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6098 -0.7715 1.5633 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6552 0.7056 -0.2508 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6976 1.5408 0.5396 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4720 0.8627 1.0537 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0373 -0.3081 0.2789 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3851 -1.5959 0.9214 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5834 0.3995 1.8191 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7595 0.5850 -0.4575 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2026 0.9346 -1.7487 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8639 -0.5805 0.7864 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4761 -1.1789 -0.3947 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9428 -1.0233 -0.6140 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5488 0.3051 -0.7614 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0213 1.1599 -1.8828 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8108 1.0392 0.5141 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9068 0.0046 -1.2372 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0139 0.8118 0.8814 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2824 1.0395 2.2280 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3296 -0.4048 2.9352 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0761 -0.3264 2.9918 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2359 -1.8732 1.3541 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8214 0.7432 -0.2406 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0968 -2.0430 -1.2473 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9626 -0.4172 -2.1598 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0727 -1.4534 -2.8357 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1806 -2.3388 -1.3078 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1884 -2.1558 -2.0027 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6382 -0.8970 0.1274 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 1.4859 -1.6970 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1141 0.2200 -2.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8255 2.3606 -0.7800 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4256 2.3820 1.4617 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2824 1.5681 2.1654 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2435 2.4316 0.6010 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5327 -1.7839 1.1624 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4869 -0.8071 2.2781 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7597 -0.4708 2.1953 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0423 1.3695 -1.0890 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4405 2.4701 -0.0117 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2722 1.9060 1.4414 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3329 1.6322 1.0679 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6159 0.5451 2.1041 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2839 -2.0415 0.3991 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5897 -1.4661 2.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3743 -2.4151 0.8432 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4816 0.2062 1.4562 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8583 0.2121 -1.3808 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1714 0.7271 -2.6235 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4464 -0.9606 1.6897 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0313 -0.7934 -1.3709 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3027 -2.2960 -0.3408 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5375 -1.5993 0.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1882 -1.5955 -1.5743 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7750 0.4977 -2.7203 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8623 1.8501 -2.1901 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2029 1.8372 -1.6060 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9230 1.2842 0.6513 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5927 0.3985 1.3825 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3359 2.0421 0.5460 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2332 -0.7709 -0.7384 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6914 1.3155 0.1258 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 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 14 23 1 0 13 24 1 0 6 25 1 6 2 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 29 32 1 0 26 33 1 0 21 3 1 0 21 6 1 0 18 7 1 0 16 11 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 1 3 38 1 6 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 8 43 1 0 11 44 1 1 12 45 1 0 12 46 1 0 13 47 1 6 14 48 1 1 15 49 1 0 15 50 1 0 17 51 1 0 17 52 1 0 17 53 1 0 18 54 1 6 19 55 1 0 19 56 1 0 20 57 1 0 20 58 1 0 22 59 1 0 22 60 1 0 22 61 1 0 23 62 1 0 24 63 1 0 25 64 1 0 26 65 1 1 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 30 70 1 0 30 71 1 0 30 72 1 0 31 73 1 0 31 74 1 0 31 75 1 0 32 76 1 0 33 77 1 0 M END

Standard InCHIKey	UPEZCKBFRMILAV-JMZLNJERSA-N
Standard InCHI	InChI=1S/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22+,23-,25+,26+,27+/m0/s1
SMILES	C[C@@H]([C@H]1CC[C@]2(C3=CC(=O)[C@@H]4C[C@H]([C@H](C[C@]4(C)[C@H]3CC[C@]12C)O)O)O)[C@@H](CCC(C)(C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	464.31	Volume:	488.791 ? Van der Waals volume.
Dense:	0.95	LogP:	1.736 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.147 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.471 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	21.0
TPSA:	118.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.427	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.065	Fsp³:	0.889
MCE-18:	84.118 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.525	Fluc inhibitor:	0.001 ? 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:	0.333	Promiscuous compounds:	0.44

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.903	MDCK Permeability:	-4.645
Pgp-inhibitor:	0.004	Pgp-substrate:	0.974
PAMPA:	0.994 ? 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):	0.0
20% Bioavailability (F20%):	0.06	30% Bioavailability (F30%):	0.041
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124	MRP1:	0.549
Plasma Protein Binding (PPB):	66.369%	Volume Distribution (VD):	0.133
Fu:	33.049% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.94	BCRP inhibitor:	0.602
BSEP inhibitor:	0.506

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.009	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.182	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.063 ? 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):

7.129

Half-life (T1/2):

2.126

ADMET: Toxicity

hERG Blockers:	0.057	hERG Blockers (10um):	0.233
Human Hepatotoxicity (H-HT):	0.747	Drug-induced Liver Injury (DILI):	0.01
AMES Toxicity:	0.194	Rat Oral Acute Toxicity:	0.171
Maximum Recommended Daily Dose:	0.777	Skin Sensitization:	0.862
Carcinogencity:	0.86	Eye Corrosion:	0.0
Eye Irritation:	0.188	Respiratory Toxicity:	0.374
Drug-induced Neurotoxicity:	0.025	Ototoxicity:	0.928
Hematotoxicity:	0.304	Drug-induced Nephrotoxicity:	0.781
Genotoxicity:	0.583	RPMI-8226 Immunitoxicity:	0.117
A549 Cytotoxicity:	0.082	Hek293 Cytotoxicity:	0.386
BCF:	0.486 ? 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:	3.23 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.886 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.883 ? 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
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39770000295]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978200]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429258]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[8945767]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO27659	Tanacetum parthenifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1776	Attalea excelsa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11032	Coutarea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13121	Crepidiastrum sonchifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11531	Duguetia calycina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7313	Epirrhoe sperryi	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO716	Greenwayodendron oliveri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5727	Hymenothrix wislizenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12858	Jacaranda chelonia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8389	Ophryosporus floribundus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12971	Payena lucida	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12516	Phalaris canariensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12411	Eriostemon spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12030	Streptomyces yokosukanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11214	Rivina humilis	Species	Petiveriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29602	Daiswa yunnanensis	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12030	Streptomyces yokosukanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11032	Coutarea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7313	Epirrhoe sperryi	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11531	Duguetia calycina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12971	Payena lucida	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO716	Greenwayodendron oliveri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8389	Ophryosporus floribundus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27659	Tanacetum parthenifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11214	Rivina humilis	Species	Petiveriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12516	Phalaris canariensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12858	Jacaranda chelonia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13121	Crepidiastrum sonchifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5727	Hymenothrix wislizenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12411	Eriostemon spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1776	Attalea excelsa	Species	Arecaceae	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	3
Ratio	1
FICI	3
Inhibition	2
Ki	2
EC50	1
Ratio CC50/EC50	1

Activity Type	# Activity
Individual protein	7
Protein complex	4
Organism	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3064	Individual protein	Ecdysone receptor	Drosophila melanogaster	IC50	=	2570.4	nM	PMID[19631551]
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	-1.9	%	PMID[23062825]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-0.57	%	PMID[23062825]
NPT3079	Protein complex	Ecdysone receptor	Nezara viridula	Ki	=	51100.0	nM	PMID[21594962]
NPT3079	Protein complex	Ecdysone receptor	Nezara viridula	IC50	=	60000.0	nM	PMID[21594962]
NPT3079	Protein complex	Ecdysone receptor	Nezara viridula	Ki	=	50400.0	nM	PMID[21594962]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	1.38	n.a.	PMID[22578055]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	FICI	=	2.31	n.a.	PMID[22578055]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	FICI	=	4.89	n.a.	PMID[22578055]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	FICI	=	12.16	n.a.	PMID[22578055]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT194	Organism	Dengue virus 2	Dengue virus 2	EC50	=	54280.0	nM	PMID[26988299]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	>	12.9	n.a.	PMID[26988299]

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 NPC150531 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	20050
0.1-0.2	26289
0.2-0.3	3438
0.3-0.4	30
0.4-0.5	8
0.5-0.6	12
0.6-0.7	21
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8421	Intermediate Similarity	NPC209502
0.8276	Intermediate Similarity	NPC149047
0.7931	Intermediate Similarity	NPC154072
0.7377	Intermediate Similarity	NPC50692
0.7377	Intermediate Similarity	NPC260268
0.7377	Intermediate Similarity	NPC152695
0.7377	Intermediate Similarity	NPC319077
0.7377	Intermediate Similarity	NPC76084
0.7377	Intermediate Similarity	NPC97202
0.7377	Intermediate Similarity	NPC601752
0.6935	Remote Similarity	NPC302607
0.6935	Remote Similarity	NPC477915
0.6825	Remote Similarity	NPC48733
0.6825	Remote Similarity	NPC171137
0.6719	Remote Similarity	NPC296945
0.6667	Remote Similarity	NPC204833
0.6562	Remote Similarity	NPC214264
0.6562	Remote Similarity	NPC475060
0.6562	Remote Similarity	NPC85829
0.6562	Remote Similarity	NPC83744
0.6515	Remote Similarity	NPC202167
0.6515	Remote Similarity	NPC49958
0.6462	Remote Similarity	NPC220229
0.6462	Remote Similarity	NPC601682
0.623	Remote Similarity	NPC603391
0.6176	Remote Similarity	NPC317210
0.6176	Remote Similarity	NPC476027
0.6143	Remote Similarity	NPC600136
0.6087	Remote Similarity	NPC207251
0.6	Remote Similarity	NPC49492
0.6	Remote Similarity	NPC266728
0.589	Remote Similarity	NPC600372
0.5821	Remote Similarity	NPC329417
0.5753	Remote Similarity	NPC109973
0.5676	Remote Similarity	NPC475041
0.5672	Remote Similarity	NPC11710
0.5672	Remote Similarity	NPC600374
0.5556	Remote Similarity	NPC326542
0.5441	Remote Similarity	NPC610677
0.5217	Remote Similarity	NPC217201
0.5217	Remote Similarity	NPC451956
0.5135	Remote Similarity	NPC250109
0.5072	Remote Similarity	NPC477916

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC150531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7011
0.1-0.2	1940
0.2-0.3	198
0.3-0.4	1
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