NPASS Compound

Natural Product: NPC157284

Natural Product ID	NPC157284
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oblongifolin C
IUPAC Name	n.a.
Synonyms	Oblongifolin C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL443681
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 107109 0 0 0 0 0 0 0 0999 V2000 7.2134 -1.8658 4.2499 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9466 -0.8521 3.1901 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8370 -0.8671 2.4569 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8215 -1.8954 2.6671 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4461 -2.7357 1.5118 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7665 -2.0947 0.3744 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4061 -0.8473 0.3556 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7189 -0.1443 -0.7668 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4250 0.4574 -0.2253 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4901 -0.5284 0.3012 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5569 -1.1146 -0.5681 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3047 -2.4976 -1.0345 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3580 -3.0843 -1.8878 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9925 -4.2154 -1.5117 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6452 -4.8943 -0.2324 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0533 -4.7889 -2.3942 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9112 -0.8891 0.0259 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0575 0.3044 0.5967 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8137 0.4938 1.7981 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9630 1.7576 2.1157 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4172 -0.4416 2.6891 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1465 -1.7710 2.7857 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8601 -2.6453 3.6274 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8833 -2.1650 4.4044 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1735 -0.8274 4.3273 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4684 0.0139 3.4994 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2125 -0.3537 5.1222 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6010 -2.9983 5.2392 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3265 1.4325 -0.0489 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3811 2.5301 0.5431 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5696 1.2906 -1.3164 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3765 1.9385 -2.3808 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7085 1.1662 -2.3793 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8600 1.7604 -2.1719 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1129 0.9900 -2.1769 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9023 3.2166 -1.9382 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5933 -0.1832 -1.7655 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6327 -0.5277 -2.8985 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8792 1.5678 -1.1747 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5316 1.3787 -2.5463 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3462 2.8237 -0.5297 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2131 4.1644 -1.0179 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0533 4.8423 -1.2745 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3528 5.3974 -2.4605 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6579 6.0676 -2.6502 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6487 5.3328 -3.5499 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9458 -1.8024 -0.0039 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5083 -2.9724 -0.8095 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9709 0.1908 2.9693 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2948 -2.8573 3.7602 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1355 -1.6662 4.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3613 -1.8748 4.9778 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7404 -0.1076 1.7160 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9307 -1.4074 3.1360 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1997 -2.5968 3.4725 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3273 -3.3428 1.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7009 -3.5027 1.8993 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5917 -0.2477 1.2684 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5239 -0.8767 -1.5525 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4155 0.6039 -1.1417 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8302 1.0005 0.7075 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1063 -1.3894 0.6928 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0342 -0.1185 1.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6128 -2.4646 -1.7052 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0429 -3.2231 -0.2528 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6383 -2.6206 -2.8263 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6666 -5.3853 -0.3459 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4446 -5.6346 -0.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6539 -4.1424 0.5929 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8854 -4.0730 -2.5736 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6137 -5.0078 -3.4028 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4692 -5.6861 -1.9294 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2915 -2.1763 2.2369 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5925 -3.6899 3.6516 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7385 1.0693 3.4733 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1804 -0.3820 4.7825 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3761 -3.5175 4.8977 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7189 2.9583 -2.2069 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0330 1.8012 -3.4182 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7361 0.1002 -2.5540 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5794 1.0979 -1.1533 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9452 -0.1059 -2.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8589 1.3788 -2.9057 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4882 3.7402 -2.8306 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9668 3.5561 -1.7532 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3535 3.5567 -1.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9304 1.9395 -3.2704 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5675 1.7863 -2.5476 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4865 0.3174 -2.7974 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9461 2.8427 0.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4737 2.6966 -0.2514 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7284 4.8695 -0.2498 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8911 4.3949 -1.9177 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7864 4.9190 -0.4832 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5428 7.1650 -2.7144 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3794 5.7869 -1.8402 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1146 5.6889 -3.6049 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9151 4.2765 -3.7287 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2026 5.7978 -4.4715 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5207 5.9432 -3.1936 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6803 -1.8112 -0.7139 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5185 -3.4620 -0.7315 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2352 -3.8427 -0.8085 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5902 -2.4830 -1.7751 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5244 1.0930 2.4807 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3966 0.4614 3.9654 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7670 -0.2602 2.3332 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 6 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 6 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 6 39 41 1 0 41 42 1 0 42 43 1 0 43 44 2 3 44 45 1 0 44 46 1 0 17 47 1 0 6 48 1 0 2 49 1 0 39 9 1 0 37 11 1 0 26 21 1 0 1 50 1 0 1 51 1 0 1 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 9 61 1 1 10 62 1 0 10 63 1 0 12 64 1 0 12 65 1 0 13 66 1 0 15 67 1 0 15 68 1 0 15 69 1 0 16 70 1 0 16 71 1 0 16 72 1 0 22 73 1 0 23 74 1 0 26 75 1 0 27 76 1 0 28 77 1 0 32 78 1 0 32 79 1 0 33 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 36 84 1 0 36 85 1 0 36 86 1 0 40 87 1 0 40 88 1 0 40 89 1 0 41 90 1 0 41 91 1 0 42 92 1 0 42 93 1 0 43 94 1 0 45 95 1 0 45 96 1 0 45 97 1 0 46 98 1 0 46 99 1 0 46100 1 0 47101 1 0 48102 1 0 48103 1 0 48104 1 0 49105 1 0 49106 1 0 49107 1 0 M END

Standard InCHIKey	XIKKSUTXFFVDEF-SSVAQFLFSA-N
Standard InCHI	InChI=1S/C43H58O6/c1-27(2)13-11-15-31(9)16-18-33-26-42(23-20-29(5)6)38(47)36(37(46)32-17-19-34(44)35(45)25-32)39(48)43(40(42)49,24-21-30(7)8)41(33,10)22-12-14-28(3)4/h13-14,16-17,19-21,25,33,44-45,47H,11-12,15,18,22-24,26H2,1-10H3/b31-16+/t33-,41+,42+,43-/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)[C@@]1(C)CCC=C(C)C)O)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	670.42	Volume:	747.718 ? Van der Waals volume.
Dense:	0.897	LogP:	8.423 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.762 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.013 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	24.0
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:	0.06	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.719	Fsp³:	0.512
MCE-18:	100.923 ? 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:	0.999	Fluc inhibitor:	0.137 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.033 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.572 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.608	Promiscuous compounds:	0.191

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.796	MDCK Permeability:	-4.667
Pgp-inhibitor:	0.144	Pgp-substrate:	0.0
PAMPA:	0.914 ? 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%):	0.008	30% Bioavailability (F30%):	0.004
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.996
Plasma Protein Binding (PPB):	90.494%	Volume Distribution (VD):	0.107
Fu:	11.406% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.954	BCRP inhibitor:	0.002
BSEP inhibitor:	0.064

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.035	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.155	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
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):

6.948

Half-life (T1/2):

1.07

ADMET: Toxicity

hERG Blockers:	0.039	hERG Blockers (10um):	0.252
Human Hepatotoxicity (H-HT):	0.822	Drug-induced Liver Injury (DILI):	0.621
AMES Toxicity:	0.163	Rat Oral Acute Toxicity:	0.744
Maximum Recommended Daily Dose:	0.171	Skin Sensitization:	0.999
Carcinogencity:	0.291	Eye Corrosion:	0.0
Eye Irritation:	0.038	Respiratory Toxicity:	0.948
Drug-induced Neurotoxicity:	0.123	Ototoxicity:	0.971
Hematotoxicity:	0.615	Drug-induced Nephrotoxicity:	0.964
Genotoxicity:	0.988	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.862	Hek293 Cytotoxicity:	0.176
BCF:	1.747 ? 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:	6.108 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	8.356 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	8.422 ? 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]
NPO40144	Garcinia schomburgkiana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27409517]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
NPO40144	Garcinia schomburgkiana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
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]
NPO10228	Ascochyta viciae	Species	Didymellaceae	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]
NPO1154	Neomeris annulata	Species	Dasycladaceae	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]

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	12
Inhibition	1

Activity Type	# Activity
Individual protein	5
Cell line	5
Others	1
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1337	Individual protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	=	7770.0	nM	PMID[27396929]
NPT1337	Individual protein	Hepatocyte growth factor receptor	Homo sapiens	Inhibition	>	50.0	%	PMID[27396929]
NPT1046	Individual protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	IC50	=	9000.0	nM	PMID[27669815]
NPT1158	Individual protein	NAD-dependent deacetylase sirtuin 2	Homo sapiens	IC50	=	22000.0	nM	PMID[27669815]
NPT3732	Individual protein	DNA polymerase lambda	Homo sapiens	IC50	=	5200.0	nM	PMID[27409517]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	12960.0	nM	PMID[27396929]
NPT196	Cell line	AGS	Homo sapiens	IC50	=	4580.0	nM	PMID[27396929]
NPT81	Cell line	A549	Homo sapiens	IC50	=	4290.0	nM	PMID[27396929]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	5830.0	nM	PMID[27396929]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	6740.0	nM	PMID[27396929]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	4460.0	nM	PMID[27396929]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	9200.0	nM	PMID[27396929]
NPT2	Others	Unspecified	n.a.	IC50	=	53000.0	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 NPC157284 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	7969
0.1-0.2	39132
0.2-0.3	2606
0.3-0.4	80
0.4-0.5	23
0.5-0.6	19
0.6-0.7	9
0.7-0.8	0
0.8-0.85	7
0.85-0.9	8
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC23667
0.9552	High Similarity	NPC5014
0.8939	High Similarity	NPC289358
0.8939	High Similarity	NPC4289
0.8939	High Similarity	NPC42384
0.863	High Similarity	NPC482617
0.863	High Similarity	NPC482616
0.8592	High Similarity	NPC25736
0.8551	High Similarity	NPC114333
0.8551	High Similarity	NPC28592
0.8429	Intermediate Similarity	NPC473479
0.8429	Intermediate Similarity	NPC50615
0.8429	Intermediate Similarity	NPC141650
0.8243	Intermediate Similarity	NPC482618
0.8169	Intermediate Similarity	NPC165191
0.8169	Intermediate Similarity	NPC177501
0.8028	Intermediate Similarity	NPC51531
0.7808	Intermediate Similarity	NPC482621
0.7639	Intermediate Similarity	NPC198803
0.7286	Intermediate Similarity	NPC149773
0.6933	Remote Similarity	NPC48949
0.6627	Remote Similarity	NPC482620
0.6538	Remote Similarity	NPC30846
0.6364	Remote Similarity	NPC46242
0.6364	Remote Similarity	NPC91887
0.6364	Remote Similarity	NPC93556
0.6329	Remote Similarity	NPC469857
0.6329	Remote Similarity	NPC245760
0.6282	Remote Similarity	NPC297797
0.5976	Remote Similarity	NPC471971
0.5976	Remote Similarity	NPC471972
0.5976	Remote Similarity	NPC469855
0.5854	Remote Similarity	NPC294330
0.5854	Remote Similarity	NPC479151
0.5732	Remote Similarity	NPC479148
0.5714	Remote Similarity	NPC469856
0.5647	Remote Similarity	NPC471970
0.5641	Remote Similarity	NPC473779
0.56	Remote Similarity	NPC259400
0.56	Remote Similarity	NPC130591
0.56	Remote Similarity	NPC234637
0.5595	Remote Similarity	NPC469854
0.5595	Remote Similarity	NPC482619
0.5412	Remote Similarity	NPC603871
0.5287	Remote Similarity	NPC479146
0.5172	Remote Similarity	NPC237441
0.5119	Remote Similarity	NPC473527
0.5063	Remote Similarity	NPC611064

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC157284 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3983
0.1-0.2	5102
0.2-0.3	65
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