NPASS Compound

Natural Product: NPC175972

Natural Product ID	NPC175972
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YCBSMEKEDOHEQI-WKQJYAATSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	40884490
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 84 88 0 0 0 0 0 0 0 0999 V2000 -5.5546 -2.9443 0.1622 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9273 -1.8134 0.9523 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5510 -0.5358 0.5002 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9834 -0.1593 -0.8241 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5018 0.2088 -0.6480 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7352 -0.0825 -1.8698 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3854 -0.6626 -1.7603 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6651 -0.5718 -0.4725 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1856 -1.9769 -0.0783 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5254 -0.1287 0.6500 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9478 0.5129 1.6541 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4785 0.8511 1.7997 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2943 0.2646 0.7115 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7194 0.7558 0.6981 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8235 2.2446 1.0225 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3821 0.0711 1.9077 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8137 0.4390 2.0535 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5873 0.5840 0.8030 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8894 0.0884 -0.4200 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0762 -1.4097 -0.4843 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6882 0.6401 -1.6153 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4613 0.5120 -0.5591 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7980 -0.5046 -1.4715 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3653 -0.2083 -1.7565 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5825 0.3270 -0.5898 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1153 1.7258 -0.9313 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7941 -0.1540 0.8978 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9909 -0.4027 0.6152 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3998 -1.8087 0.7981 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8583 -2.4143 2.0636 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5256 1.7009 -0.4112 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0917 2.2357 0.6164 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0635 2.5369 -1.3963 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1117 3.9385 -1.2291 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3806 -2.5834 -0.4925 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8058 -3.4236 -0.5257 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9912 -3.7280 0.8152 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2302 -1.9744 2.0116 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6407 -0.7235 0.3594 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4826 0.2914 1.2348 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5310 0.6757 -1.2840 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0079 -1.0200 -1.5031 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7567 0.8483 -2.5151 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3608 -0.7940 -2.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3820 -1.7344 -2.1354 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7512 -0.1549 -2.5519 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1850 -2.1263 1.0198 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8620 -2.7516 -0.5139 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8137 -2.2134 -0.4306 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6393 0.8251 2.4759 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7929 0.5101 2.8198 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5027 1.9840 1.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3790 -0.8408 0.9554 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9738 2.8367 0.7043 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7823 2.6584 0.5876 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9352 2.4275 2.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1514 -0.9934 1.9536 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8439 0.5340 2.7907 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9517 1.3900 2.6487 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2910 -0.3455 2.7014 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9345 1.6210 0.5935 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1482 -1.6048 -0.1845 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4623 -1.9782 0.2049 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9827 -1.8243 -1.4958 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6547 0.0596 -1.6058 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8816 1.7211 -1.4993 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2101 0.4147 -2.5682 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4682 1.4675 -1.1662 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9973 -1.5420 -1.1419 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3503 -0.4135 -2.4552 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9454 -1.1744 -2.1686 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2974 0.4932 -2.6413 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2322 2.3037 -0.0520 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9406 2.3296 -1.3890 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6547 1.6805 -1.7315 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4540 0.2137 0.2645 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4580 0.1893 1.4595 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1957 -2.4714 -0.0610 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3037 -3.3508 1.8115 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1195 -1.7604 2.5692 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6425 -2.7212 2.7856 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5346 4.2224 -0.3161 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6987 4.4525 -2.1296 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1634 4.2388 -1.0376 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 1 0 8 9 1 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 18 27 1 0 10 28 1 0 28 29 1 0 29 30 1 0 5 31 1 1 31 32 2 0 31 33 1 0 33 34 1 0 29 2 1 0 28 5 1 0 25 8 1 0 25 13 1 0 22 14 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 1 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 6 43 1 0 6 44 1 0 7 45 1 0 7 46 1 0 9 47 1 0 9 48 1 0 9 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 13 53 1 1 15 54 1 0 15 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 6 20 62 1 0 20 63 1 0 20 64 1 0 21 65 1 0 21 66 1 0 21 67 1 0 22 68 1 6 23 69 1 0 23 70 1 0 24 71 1 0 24 72 1 0 26 73 1 0 26 74 1 0 26 75 1 0 27 76 1 0 28 77 1 1 29 78 1 6 30 79 1 0 30 80 1 0 30 81 1 0 34 82 1 0 34 83 1 0 34 84 1 0 M END

Standard InCHIKey	YCBSMEKEDOHEQI-WKQJYAATSA-N
Standard InCHI	InChI=1S/C31H50O3/c1-19-11-16-31(26(33)34-8)18-17-29(6)21(25(31)20(19)2)9-10-23-28(5)14-13-24(32)27(3,4)22(28)12-15-30(23,29)7/h9,19-20,22-25,32H,10-18H2,1-8H3/t19-,20+,22-,23-,24-,25+,28+,29-,30-,31+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](C(C)(C)[C@H]5CC[C@@]34C)O)[C@@H]2[C@H]1C)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.38	Volume:	523.047 ? Van der Waals volume.
Dense:	0.899	LogP:	5.78 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.51 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.077 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.326	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.746	Fsp³:	0.903
MCE-18:	101.763 ? 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:	0.907	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.086 ? 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:	0.335	Promiscuous compounds:	0.168

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.237	MDCK Permeability:	-4.878
Pgp-inhibitor:	0.57	Pgp-substrate:	0.04
PAMPA:	0.64 ? 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%):	0.094	30% Bioavailability (F30%):	0.07
50% Bioavailability (F50%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.317	MRP1:	0.175
Plasma Protein Binding (PPB):	92.494%	Volume Distribution (VD):	-0.107
Fu:	9.208% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.881
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.047	CYP1A2-substrate:	0.348
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.01	CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.275	CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.987
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.967
HLM stability:	0.891 ? 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):

11.744

Half-life (T1/2):

0.627

ADMET: Toxicity

hERG Blockers:	0.058	hERG Blockers (10um):	0.151
Human Hepatotoxicity (H-HT):	0.519	Drug-induced Liver Injury (DILI):	0.132
AMES Toxicity:	0.199	Rat Oral Acute Toxicity:	0.28
Maximum Recommended Daily Dose:	0.593	Skin Sensitization:	0.623
Carcinogencity:	0.854	Eye Corrosion:	0.022
Eye Irritation:	0.576	Respiratory Toxicity:	0.901
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.499
Hematotoxicity:	0.431	Drug-induced Nephrotoxicity:	0.645
Genotoxicity:	0.245	RPMI-8226 Immunitoxicity:	0.053
A549 Cytotoxicity:	0.276	Hek293 Cytotoxicity:	0.373
BCF:	2.459 ? 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:	4.467 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.5 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.191 ? 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
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[10661881]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11430011]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	stems	n.a.	n.a.	PMID[12350169]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387673]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[28294414]
NPO16125	Micromonas pusilla	Species	Mamiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15349	Acacia sparsiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14936	Agave shawii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15205	Alaria crispa	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9479	Ambrosia grayi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13139	Anatheca montagnei	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11808	Ania latifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14807	Arenaria juncea	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11436	Baeomyces roseus	Species	Baeomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5866	Bitis arietans	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14463	Dirca occidentalis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15797	Drypetes littoralis	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13442	Eucalyptus regnans	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12293	Euphorbia iberica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24409	Evasterias troschelii	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5047	Evodiopanax innovans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO820	Grindelia perennis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11002	Hopea jucunda	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12490	Lecidea speirodes	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2038	Myrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14313	Pachybasium candidum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16718	Pinna nobilis	Species	Pinnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16475	Plumbago pulchella	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2827	Plumeria alba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16557	Polygala ruwenzoriensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8804	Raputia simulans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20219	Rhizobium etli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27733	Rosa hybrid cultivar	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16796	Rumex conglomeratus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4589	Sarcotragus spinosulus	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15588	Senecio desfontainei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11987	Silene inflata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11994	Thesium humile	Species	Thesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16025	Werneria decora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16125	Micromonas pusilla	Species	Mamiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13139	Anatheca montagnei	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11994	Thesium humile	Species	Thesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14936	Agave shawii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4589	Sarcotragus spinosulus	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9479	Ambrosia grayi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15797	Drypetes littoralis	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11002	Hopea jucunda	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11987	Silene inflata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16718	Pinna nobilis	Species	Pinnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11436	Baeomyces roseus	Species	Baeomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16557	Polygala ruwenzoriensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16796	Rumex conglomeratus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15588	Senecio desfontainei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14463	Dirca occidentalis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5866	Bitis arietans	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27733	Rosa hybrid cultivar	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14313	Pachybasium candidum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15205	Alaria crispa	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11808	Ania latifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24409	Evasterias troschelii	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14807	Arenaria juncea	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8804	Raputia simulans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16025	Werneria decora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16475	Plumbago pulchella	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12490	Lecidea speirodes	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5047	Evodiopanax innovans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15349	Acacia sparsiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12293	Euphorbia iberica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13442	Eucalyptus regnans	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2038	Myrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20219	Rhizobium etli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO820	Grindelia perennis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2827	Plumeria alba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC175972 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	18624
0.1-0.2	25626
0.2-0.3	4516
0.3-0.4	837
0.4-0.5	175
0.5-0.6	50
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC40552
0.7869	Intermediate Similarity	NPC307335
0.7869	Intermediate Similarity	NPC74855
0.7679	Intermediate Similarity	NPC27765
0.7679	Intermediate Similarity	NPC122418
0.7679	Intermediate Similarity	NPC491014
0.7627	Intermediate Similarity	NPC95594
0.7541	Intermediate Similarity	NPC477579
0.7167	Intermediate Similarity	NPC40394
0.7143	Intermediate Similarity	NPC272075
0.7097	Intermediate Similarity	NPC246708
0.7097	Intermediate Similarity	NPC606009
0.6984	Remote Similarity	NPC127855
0.6721	Remote Similarity	NPC132478
0.6714	Remote Similarity	NPC171208
0.65	Remote Similarity	NPC120098
0.625	Remote Similarity	NPC470588
0.6061	Remote Similarity	NPC610552
0.6029	Remote Similarity	NPC488519
0.5968	Remote Similarity	NPC290598
0.5968	Remote Similarity	NPC30590
0.5857	Remote Similarity	NPC49776
0.5857	Remote Similarity	NPC63118
0.5857	Remote Similarity	NPC474436
0.5846	Remote Similarity	NPC235341
0.5846	Remote Similarity	NPC291379
0.5758	Remote Similarity	NPC602872
0.5652	Remote Similarity	NPC610937
0.5634	Remote Similarity	NPC98874
0.5606	Remote Similarity	NPC290495
0.5571	Remote Similarity	NPC51700
0.5571	Remote Similarity	NPC259788
0.5571	Remote Similarity	NPC88716
0.5571	Remote Similarity	NPC255589
0.5571	Remote Similarity	NPC68160
0.5571	Remote Similarity	NPC195019
0.5556	Remote Similarity	NPC110139
0.5556	Remote Similarity	NPC108709
0.5542	Remote Similarity	NPC477292
0.5493	Remote Similarity	NPC18872
0.5493	Remote Similarity	NPC290614
0.5455	Remote Similarity	NPC191763
0.5455	Remote Similarity	NPC101475
0.5443	Remote Similarity	NPC46388
0.5429	Remote Similarity	NPC86372
0.5429	Remote Similarity	NPC136313
0.5385	Remote Similarity	NPC82477
0.5352	Remote Similarity	NPC171203
0.5352	Remote Similarity	NPC307426
0.5352	Remote Similarity	NPC98442
0.5352	Remote Similarity	NPC242468
0.5316	Remote Similarity	NPC167383
0.5286	Remote Similarity	NPC479748
0.5217	Remote Similarity	NPC234617
0.5211	Remote Similarity	NPC214756
0.5211	Remote Similarity	NPC304285
0.5211	Remote Similarity	NPC329943
0.5205	Remote Similarity	NPC164349
0.5161	Remote Similarity	NPC101744
0.5143	Remote Similarity	NPC48756
0.5139	Remote Similarity	NPC7260
0.5139	Remote Similarity	NPC210037
0.5139	Remote Similarity	NPC120968
0.5139	Remote Similarity	NPC227467
0.5139	Remote Similarity	NPC273621
0.5139	Remote Similarity	NPC112866
0.5114	Remote Similarity	NPC179434
0.5072	Remote Similarity	NPC292015
0.507	Remote Similarity	NPC477872

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC175972 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7003
0.1-0.2	2080
0.2-0.3	62
0.3-0.4	3
0.4-0.5	2
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