NPASS Compound

Natural Product: NPC188031

Natural Product ID	NPC188031
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NTZPAQLJAUNIKO-HOHUBLMVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101630504
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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 87 90 0 0 0 0 0 0 0 0999 V2000 6.3855 2.0808 -0.9555 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8729 0.6819 -0.9101 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8459 -0.3927 -0.9207 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9027 -0.2733 0.2907 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8810 -1.3556 0.2712 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9241 -1.4755 1.3503 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7623 -1.6954 2.6431 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 -0.5897 1.7012 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0517 0.8131 2.0896 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7046 1.5383 1.8890 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2525 0.3659 1.6727 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4282 -0.2412 3.0399 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5051 0.6957 0.9757 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6940 0.8207 1.9389 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9660 1.1969 1.1827 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2506 0.0763 0.2038 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6399 0.0348 -0.3060 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4013 1.2629 0.2183 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4203 -1.1606 0.2648 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8034 0.0149 -1.7796 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7355 -0.6653 -2.5558 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4947 -1.0152 -1.8206 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1736 0.0642 -0.8210 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9349 1.3343 -1.5366 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9110 -0.2788 -0.0494 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2445 -1.3778 -0.3153 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0050 -1.7497 0.4031 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6759 -0.4750 0.7762 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0687 0.3424 -0.4105 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0428 1.3329 -2.2394 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0894 -0.4850 -2.1846 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1790 -1.5447 -3.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1897 0.6155 -2.6215 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3133 2.2395 -0.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9742 2.7206 -0.2416 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6701 2.5006 -1.9669 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5964 0.4609 -1.7485 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5094 0.5517 0.0127 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4245 -1.3636 -0.8303 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3753 0.7014 0.0648 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5311 -0.2465 1.1764 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4385 -1.4605 -0.7719 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4932 -2.3210 0.3056 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4504 -2.5185 1.2405 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2604 -0.7317 2.8890 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4537 -2.5304 2.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0863 -1.9226 3.4921 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3810 -1.0912 2.6232 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2497 0.8814 3.2013 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8102 1.4089 1.6155 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3691 2.0407 2.8133 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7201 2.2540 1.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3715 0.1694 3.5083 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5757 -1.3263 3.0527 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3350 0.1244 3.7913 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3936 1.7287 0.5627 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5607 1.5825 2.6994 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9277 -0.2077 2.3157 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9382 2.1881 0.7491 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7760 1.1698 1.9414 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0962 -0.8652 0.8189 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8569 2.1855 0.0178 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3576 1.2957 -0.3558 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7029 1.1192 1.2795 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4959 -0.9084 0.3094 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2975 -2.0101 -0.4408 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0164 -1.4692 1.2392 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7745 -0.5143 -2.0179 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1067 -1.6186 -3.0388 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5091 -0.0058 -3.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6334 -2.0122 -1.3582 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6543 -1.0822 -2.5491 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6193 2.1611 -1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9161 1.7519 -1.4060 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0499 1.2399 -2.6583 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6128 -2.0684 -1.1032 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1424 -2.4505 1.2212 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6598 -2.2644 -0.3575 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8510 1.1111 -0.1536 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4014 -0.3078 -1.2636 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2406 0.9457 -0.8333 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9838 1.5410 -2.3449 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6427 -1.6404 -3.9233 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8377 -2.3424 -2.6911 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5261 0.9693 -1.8124 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5008 0.2818 -3.4398 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7720 1.4595 -3.0771 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 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 6 20 30 1 0 3 31 1 0 31 32 2 0 31 33 1 0 28 8 1 0 28 11 1 0 25 13 1 0 23 16 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 0 2 38 1 0 3 39 1 1 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 6 44 1 6 7 45 1 0 7 46 1 0 7 47 1 0 8 48 1 1 9 49 1 0 9 50 1 0 10 51 1 0 10 52 1 0 12 53 1 0 12 54 1 0 12 55 1 0 13 56 1 6 14 57 1 0 14 58 1 0 15 59 1 0 15 60 1 0 16 61 1 1 18 62 1 0 18 63 1 0 18 64 1 0 19 65 1 0 19 66 1 0 19 67 1 0 20 68 1 1 21 69 1 0 21 70 1 0 22 71 1 0 22 72 1 0 24 73 1 0 24 74 1 0 24 75 1 0 26 76 1 0 27 77 1 0 27 78 1 0 29 79 1 0 29 80 1 0 29 81 1 0 30 82 1 0 32 83 1 0 32 84 1 0 33 85 1 0 33 86 1 0 33 87 1 0 M END

Standard InCHIKey	NTZPAQLJAUNIKO-HOHUBLMVSA-N
Standard InCHI	InChI=1S/C32H54O/c1-10-23(21(2)3)12-11-22(4)24-15-19-32(9)26-13-14-27-29(5,6)28(33)17-18-30(27,7)25(26)16-20-31(24,32)8/h16,22-24,26-28,33H,2,10-15,17-20H2,1,3-9H3/t22-,23+,24-,26-,27+,28+,30-,31-,32+/m1/s1
SMILES	CC[C@@H](CC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@]12C)O)C(=C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.42	Volume:	531.319 ? Van der Waals volume.
Dense:	0.855	LogP:	7.146 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.926 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.228 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	21.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.397	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.833	Fsp³:	0.875
MCE-18:	80.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.94	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.752	Promiscuous compounds:	0.184

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.153	MDCK Permeability:	-4.902
Pgp-inhibitor:	0.115	Pgp-substrate:	0.002
PAMPA:	0.123 ? 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%):	0.046	30% Bioavailability (F30%):	0.447
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.455	MRP1:	0.018
Plasma Protein Binding (PPB):	95.744%	Volume Distribution (VD):	-0.04
Fu:	3.935% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.988
BSEP inhibitor:	0.062

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.61
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.311
CYP2D6-inhibitor:	0.128	CYP2D6-substrate:	0.676
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.995 ? 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):

13.698

Half-life (T1/2):

0.495

ADMET: Toxicity

hERG Blockers:	0.048	hERG Blockers (10um):	0.301
Human Hepatotoxicity (H-HT):	0.47	Drug-induced Liver Injury (DILI):	0.045
AMES Toxicity:	0.158	Rat Oral Acute Toxicity:	0.218
Maximum Recommended Daily Dose:	0.608	Skin Sensitization:	0.936
Carcinogencity:	0.64	Eye Corrosion:	0.289
Eye Irritation:	0.941	Respiratory Toxicity:	0.632
Drug-induced Neurotoxicity:	0.077	Ototoxicity:	0.479
Hematotoxicity:	0.357	Drug-induced Nephrotoxicity:	0.437
Genotoxicity:	0.021	RPMI-8226 Immunitoxicity:	0.095
A549 Cytotoxicity:	0.179	Hek293 Cytotoxicity:	0.286
BCF:	3.22 ? 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:	5.035 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.535 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.861 ? 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
NPO15351	Streptomyces prunicolor	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	DOI[10.1021/np50098a008]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	roots	n.a.	n.a.	PMID[12444706]
NPO11898	Lobophora variegata	Species	Dictyotaceae	Eukaryota	n.a.	at depths of 630 m at El Mdano (Tenerife, Canary Islands)	n.a.	PMID[26126835]
NPO5247	Elaphoglossum lindbergii	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26689830]
NPO2996	Pistacia atlantica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38202742]
NPO9606	Castanea dentata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15351	Streptomyces prunicolor	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1116	Periconia atropurpurea	Species	Periconiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10530	Aconitum subcuneatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1044	Caiman crocodilus	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5247	Elaphoglossum lindbergii	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9363	Ferula ammoniacum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2207	Sphaerella rubella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11206	Trifolium hybridum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7560	Tachardia acaciae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12146	Stemodia maritima	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11527	Ibacus peronii	Species	Scyllaridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5714	Rogeria adenophylla	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12633	Rapanea neurophylla	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2996	Pistacia atlantica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23883	Penicillium abidjanum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11898	Lobophora variegata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12853	Leucocarpus perfoliatus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12853	Leucocarpus perfoliatus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12633	Rapanea neurophylla	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10530	Aconitum subcuneatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11206	Trifolium hybridum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12633	Rapanea neurophylla	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12853	Leucocarpus perfoliatus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10530	Aconitum subcuneatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10530	Aconitum subcuneatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11527	Ibacus peronii	Species	Scyllaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15351	Streptomyces prunicolor	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12633	Rapanea neurophylla	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2996	Pistacia atlantica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7560	Tachardia acaciae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9606	Castanea dentata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11206	Trifolium hybridum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12146	Stemodia maritima	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23883	Penicillium abidjanum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12853	Leucocarpus perfoliatus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1044	Caiman crocodilus	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10530	Aconitum subcuneatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11898	Lobophora variegata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5714	Rogeria adenophylla	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5247	Elaphoglossum lindbergii	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9363	Ferula ammoniacum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2207	Sphaerella rubella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1116	Periconia atropurpurea	Species	Periconiaceae	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 NPC188031 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	24935
0.1-0.2	21301
0.2-0.3	3209
0.3-0.4	375
0.4-0.5	35
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	Natural Product ID
0.5593	Remote Similarity	NPC200243

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC188031 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7982
0.1-0.2	1092
0.2-0.3	72
0.3-0.4	4
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