NPASS Compound

Natural Product: NPC114333

Natural Product ID	NPC114333
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oblongifolin B
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL505370
PubChem CID	NA
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

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 94 96 0 0 0 0 0 0 0 0999 V2000 5.8222 3.9092 -0.4498 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0944 2.4862 -0.1237 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4209 1.5050 -0.7093 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6869 0.0638 -0.3884 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4815 -0.6353 0.1543 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3361 -0.6160 -0.8234 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2121 -0.0378 -0.4492 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0164 0.0519 -1.2973 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2609 -0.4616 -0.7381 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6287 0.2681 0.5302 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8775 -0.1803 1.1802 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9189 0.2568 2.6095 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8601 1.7061 2.8244 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9336 2.3497 3.5218 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1515 1.5670 4.1531 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9398 3.8247 3.6942 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1398 0.2348 0.5099 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2546 -0.0912 -0.7578 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7689 0.8163 -1.7438 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9293 0.2654 -2.9154 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1222 2.1807 -1.6570 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9247 2.7503 -2.6774 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2470 4.0723 -2.7228 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7859 4.9139 -1.7466 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0033 4.3969 -0.7409 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6806 3.0531 -0.7045 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5576 5.2910 0.2292 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1310 6.2548 -1.8177 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7531 -1.4456 -1.1713 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0894 -1.9216 -2.2810 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8428 -2.2450 -0.2606 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2488 -3.6941 -0.3476 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5125 -4.6483 0.4642 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8183 -5.6778 0.0309 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1043 -6.5834 0.9791 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7198 -5.9973 -1.4037 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0041 -1.7090 1.1096 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2143 -2.3480 2.1005 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4063 -1.9583 -0.6578 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0945 -2.5563 -2.0146 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4870 -2.5460 0.4109 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1563 0.9094 1.1352 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4545 -1.1995 -2.1664 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1500 2.1596 0.8862 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2969 4.4059 0.4032 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2743 4.0183 -1.4075 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7865 4.4631 -0.5830 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6648 1.7829 -1.4338 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4637 0.0435 0.4038 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1359 -0.4618 -1.2652 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7499 -1.6631 0.3955 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1985 -0.1320 1.1008 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1544 0.4068 0.5520 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2337 -0.3381 -2.3214 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8859 1.1699 -1.4955 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0456 -0.1506 -1.5066 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2157 0.2894 1.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7775 1.3454 0.2214 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0965 -0.2422 3.1787 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8794 -0.1062 3.0357 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6409 2.3574 2.3863 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7615 2.2552 4.7724 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2179 0.7001 4.7397 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8508 1.2387 3.3311 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3036 4.2664 2.7278 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0262 4.2276 3.9941 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7373 4.0957 4.4374 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2965 2.0974 -3.4530 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8747 4.4574 -3.5411 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0258 2.7499 0.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1544 6.0420 0.5513 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0003 6.6239 -1.4314 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3585 -4.0608 -1.3918 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3212 -3.6953 0.0762 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5647 -4.5082 1.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8213 -7.3556 1.3453 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7442 -7.0954 0.4930 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2869 -6.0509 1.8648 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1308 -5.4129 -1.8571 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6337 -5.8227 -1.9815 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4377 -7.0750 -1.5660 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0135 -1.7972 -2.8036 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8781 -3.2556 -2.3763 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 -3.1311 -1.9059 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2308 -1.7952 0.7671 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9979 -3.4783 0.0899 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1137 -2.7807 1.2990 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0019 0.5048 1.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5365 -1.4393 -2.4195 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1215 -0.5164 -2.9948 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9338 -2.1450 -2.3046 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9852 1.5760 0.4257 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5661 3.0767 1.3198 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7077 1.5806 1.7396 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 12 13 1 0 13 14 2 3 14 15 1 0 14 16 1 0 11 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 24 28 1 0 18 29 1 0 29 30 2 0 29 31 1 0 31 32 1 1 32 33 1 0 33 34 2 3 34 35 1 0 34 36 1 0 31 37 1 0 37 38 2 0 31 39 1 0 39 40 1 0 39 41 1 0 17 42 1 0 6 43 1 0 2 44 1 0 39 9 1 0 37 11 1 0 26 21 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 5 51 1 0 5 52 1 0 7 53 1 0 8 54 1 0 8 55 1 0 9 56 1 6 10 57 1 0 10 58 1 0 12 59 1 0 12 60 1 0 13 61 1 0 15 62 1 0 15 63 1 0 15 64 1 0 16 65 1 0 16 66 1 0 16 67 1 0 22 68 1 0 23 69 1 0 26 70 1 0 27 71 1 0 28 72 1 0 32 73 1 0 32 74 1 0 33 75 1 0 35 76 1 0 35 77 1 0 35 78 1 0 36 79 1 0 36 80 1 0 36 81 1 0 40 82 1 0 40 83 1 0 40 84 1 0 41 85 1 0 41 86 1 0 41 87 1 0 42 88 1 0 43 89 1 0 43 90 1 0 43 91 1 0 44 92 1 0 44 93 1 0 44 94 1 0 M END

Standard InCHIKey	KRJWRFOMKSOZGO-KMIQQCGBSA-N
Standard InCHI	InChI=1S/C38H50O6/c1-23(2)11-10-12-26(7)13-15-28-22-37(19-17-24(3)4)33(42)31(32(41)27-14-16-29(39)30(40)21-27)34(43)38(35(37)44,36(28,8)9)20-18-25(5)6/h11,13-14,16-18,21,28,39-40,42H,10,12,15,19-20,22H2,1-9H3/b26-13+/t28-,37+,38-/m1/s1
SMILES	CC(=CCC/C(=C/C[C@@H]1C[C@@]2(CC=C(C)C)C(=C(C(=O)c3ccc(c(c3)O)O)C(=O)[C@](CC=C(C)C)(C2=O)C1(C)C)O)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.36	Volume:	663.875 ? Van der Waals volume.
Dense:	0.907	LogP:	7.118 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.093 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.461 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	23.0
TPSA:	111.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.077	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.371	Fsp³:	0.5
MCE-18:	98.439 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.997	Fluc inhibitor:	0.129 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.068 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.585 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.627	Promiscuous compounds:	0.219

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.821	MDCK Permeability:	-4.685
Pgp-inhibitor:	0.015	Pgp-substrate:	0.0
PAMPA:	0.952 ? 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%):	0.026	30% Bioavailability (F30%):	0.004
50% Bioavailability (F50%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.994
Plasma Protein Binding (PPB):	88.726%	Volume Distribution (VD):	0.101
Fu:	14.032% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.678	BCRP inhibitor:	0.0
BSEP inhibitor:	0.04

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.997
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.353
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.131	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.985
HLM stability:	1.0 ? 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):

6.271

Half-life (T1/2):

1.156

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.162
Human Hepatotoxicity (H-HT):	0.791	Drug-induced Liver Injury (DILI):	0.728
AMES Toxicity:	0.341	Rat Oral Acute Toxicity:	0.845
Maximum Recommended Daily Dose:	0.353	Skin Sensitization:	0.999
Carcinogencity:	0.373	Eye Corrosion:	0.0
Eye Irritation:	0.032	Respiratory Toxicity:	0.927
Drug-induced Neurotoxicity:	0.087	Ototoxicity:	0.949
Hematotoxicity:	0.7	Drug-induced Nephrotoxicity:	0.979
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.054
A549 Cytotoxicity:	0.859	Hek293 Cytotoxicity:	0.281
BCF:	1.753 ? 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:	5.826 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	8.075 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.924 ? 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
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(74)80113-5]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1071/CH03175]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10361686]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724839]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113969]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20058933]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	leaves	Bobai, Guangxi Province, China	2005-Dec	PMID[24679044]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	Barks	n.a.	n.a.	PMID[24754786]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26341	Trifolium resupinatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15242	Setosphaeria holmii	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9298	Piper wightii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1154	Neomeris annulata	Species	Dasycladaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2812	Lecanora kukunorensis	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6948	Davidsoniella virescens	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10228	Ascochyta viciae	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15242	Setosphaeria holmii	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1154	Neomeris annulata	Species	Dasycladaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9298	Piper wightii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26341	Trifolium resupinatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2812	Lecanora kukunorensis	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6948	Davidsoniella virescens	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6775	Cistanche salsa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10228	Ascochyta viciae	Species	Didymellaceae	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
Inhibition	1
IC50	4

Activity Type	# Activity
Cell line	3
Others	2

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
NPT393	Cell line	HCT-116	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[32791400]
NPT515	Cell line	SGC-7901	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[32791400]
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[32791400]
NPT2	Others	Unspecified	n.a.	Inhibition	=	7.0	%	PMID[16724839]
NPT2	Others	Unspecified	n.a.	IC50	=	69000.0	nM	PMID[16724839]

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 NPC114333 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	7647
0.1-0.2	39533
0.2-0.3	2534
0.3-0.4	66
0.4-0.5	29
0.5-0.6	4
0.6-0.7	19
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC28592
0.9844	High Similarity	NPC473479
0.9844	High Similarity	NPC50615
0.9844	High Similarity	NPC141650
0.9538	High Similarity	NPC165191
0.9538	High Similarity	NPC177501
0.9385	High Similarity	NPC51531
0.8594	High Similarity	NPC149773
0.8551	High Similarity	NPC23667
0.8551	High Similarity	NPC157284
0.8169	Intermediate Similarity	NPC5014
0.7639	Intermediate Similarity	NPC30846
0.7571	Intermediate Similarity	NPC289358
0.7571	Intermediate Similarity	NPC4289
0.7571	Intermediate Similarity	NPC42384
0.7465	Intermediate Similarity	NPC46242
0.7465	Intermediate Similarity	NPC91887
0.7465	Intermediate Similarity	NPC93556
0.7403	Intermediate Similarity	NPC482617
0.7403	Intermediate Similarity	NPC482616
0.7397	Intermediate Similarity	NPC469857
0.7397	Intermediate Similarity	NPC245760
0.7361	Intermediate Similarity	NPC297797
0.7333	Intermediate Similarity	NPC25736
0.7051	Intermediate Similarity	NPC482618
0.6974	Remote Similarity	NPC471971
0.6974	Remote Similarity	NPC471972
0.6974	Remote Similarity	NPC469855
0.6667	Remote Similarity	NPC259400
0.6667	Remote Similarity	NPC130591
0.6667	Remote Similarity	NPC234637
0.6623	Remote Similarity	NPC482621
0.6456	Remote Similarity	NPC469856
0.6447	Remote Similarity	NPC198803
0.641	Remote Similarity	NPC294330
0.641	Remote Similarity	NPC479151
0.6375	Remote Similarity	NPC471970
0.6329	Remote Similarity	NPC469854
0.6329	Remote Similarity	NPC603871
0.6282	Remote Similarity	NPC479148
0.619	Remote Similarity	NPC482620
0.6049	Remote Similarity	NPC237441
0.6027	Remote Similarity	NPC611064
0.6	Remote Similarity	NPC473779
0.5823	Remote Similarity	NPC48949
0.5783	Remote Similarity	NPC479146
0.5625	Remote Similarity	NPC473527
0.5176	Remote Similarity	NPC482619

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC114333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3736
0.1-0.2	5346
0.2-0.3	68
0.3-0.4	0
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