NPASS Compound

Natural Product: NPC165330

Natural Product ID	NPC165330
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UEWPQEARKYIFFJ-ANMVGWMBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	179304
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 100101 0 0 0 0 0 0 0 0999 V2000 8.9637 3.7667 0.1402 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5867 2.7494 -0.8799 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3014 2.3901 -1.0676 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2796 3.0351 -0.2325 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5777 2.1887 0.7700 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8364 1.0564 0.2134 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6574 0.0256 -0.5107 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9698 0.3258 1.2156 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9717 1.1511 1.9257 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7284 0.2745 1.9044 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2378 -1.0022 1.3528 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8830 -1.7782 2.5139 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2333 -1.9053 0.7161 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5271 -1.2672 -0.4416 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4724 -2.1004 -1.1154 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6501 -2.6335 -0.4184 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6402 -1.6731 0.1638 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9384 -2.5150 0.4942 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2845 -1.0382 1.4322 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2168 0.1983 1.4057 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2990 0.4475 -0.0578 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5475 1.2188 -0.4803 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4960 1.5503 -1.9509 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5990 2.4861 0.3043 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7672 3.3732 0.0271 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0686 2.7522 0.2919 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0329 2.5853 -0.5936 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8837 3.0291 -1.9953 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3152 1.9349 -0.1974 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6396 0.3874 -0.2346 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1341 -0.7385 -0.7415 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4421 -3.3758 -1.4075 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7389 -4.7149 -1.2234 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3240 -5.3078 -0.1956 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5336 -5.5078 -2.1854 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8802 -3.1135 0.3253 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 -4.3536 0.8694 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7017 -4.4253 1.7406 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3506 -5.5125 0.3449 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2831 -0.6633 0.5149 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9170 1.5857 -0.7326 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6436 2.1122 -1.7152 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0696 3.7738 0.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5896 4.7838 -0.1232 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5443 3.4185 1.1190 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1111 1.6642 -1.8550 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5147 3.5756 -0.8961 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7785 3.9308 0.2621 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8565 2.8932 1.3005 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3331 1.8320 1.5425 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3661 -1.0203 -0.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5402 0.0240 -1.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7399 0.0545 -0.2768 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6253 -0.1822 1.9478 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7478 2.1255 1.4561 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2691 1.3837 2.9749 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3961 0.1560 2.9701 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9473 0.7886 1.3262 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5881 -2.4948 2.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3499 -1.1047 3.2464 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0711 -2.3795 2.9725 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4954 -2.1839 1.4859 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1965 -0.2571 -0.2196 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3763 -1.1475 -1.2261 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0163 -2.9627 -1.6943 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8797 -1.4623 -1.9777 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4340 -3.3862 0.3651 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6083 -1.8235 0.9919 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2801 -2.9730 -0.4316 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6118 -3.3170 1.1868 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2605 -0.6672 1.4552 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5322 -1.6556 2.3320 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1317 -0.0985 1.9097 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6817 1.0358 1.9216 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4001 1.0804 -0.3237 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3189 1.0514 -2.5122 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5775 2.6344 -2.1585 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4964 1.2544 -2.3573 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6749 3.0677 0.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4726 2.2522 1.3805 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6256 4.2809 0.6890 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7587 3.7817 -0.9942 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2476 2.4008 1.3089 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3606 2.2926 -2.6298 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4378 4.0560 -2.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9001 3.1371 -2.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1989 2.5755 -0.4129 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4198 0.9311 -0.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3433 1.7257 0.9017 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7713 0.3893 0.7627 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9269 -4.8963 -3.0037 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8475 -6.3027 -2.5925 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3005 -6.0671 -1.6178 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2616 -5.5256 -0.7542 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9353 -6.4774 0.7098 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3787 -5.4304 0.7219 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6289 2.4671 -0.3832 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2252 1.2499 -2.2693 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5479 1.8523 -1.1412 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9476 2.8961 -2.4647 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 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 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 25 26 1 0 26 27 2 3 27 28 1 0 27 29 1 0 22 30 1 6 21 31 1 0 16 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 13 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 11 40 1 0 6 41 1 6 2 42 1 0 40 8 1 0 31 17 1 0 1 43 1 0 1 44 1 0 1 45 1 0 3 46 1 0 4 47 1 0 4 48 1 0 5 49 1 0 5 50 1 0 7 51 1 0 7 52 1 0 7 53 1 0 8 54 1 1 9 55 1 0 9 56 1 0 10 57 1 0 10 58 1 0 12 59 1 0 12 60 1 0 12 61 1 0 13 62 1 1 14 63 1 0 14 64 1 0 15 65 1 0 15 66 1 0 16 67 1 1 18 68 1 0 18 69 1 0 18 70 1 0 19 71 1 0 19 72 1 0 20 73 1 0 20 74 1 0 21 75 1 6 23 76 1 0 23 77 1 0 23 78 1 0 24 79 1 0 24 80 1 0 25 81 1 0 25 82 1 0 26 83 1 0 28 84 1 0 28 85 1 0 28 86 1 0 29 87 1 0 29 88 1 0 29 89 1 0 30 90 1 0 35 91 1 0 35 92 1 0 35 93 1 0 39 94 1 0 39 95 1 0 39 96 1 0 41 97 1 0 42 98 1 0 42 99 1 0 42100 1 0 M END

Standard InCHIKey	UEWPQEARKYIFFJ-ANMVGWMBSA-N
Standard InCHI	InChI=1S/C34H58O8/c1-23(2)13-11-19-31(7,37)27-17-21-33(9,41-27)29(39-25(5)35)15-16-30(40-26(6)36)34(10)22-18-28(42-34)32(8,38)20-12-14-24(3)4/h13-14,27-30,37-38H,11-12,15-22H2,1-10H3/t27-,28-,29-,30+,31+,32+,33+,34-/m1/s1
SMILES	CC(=CCC[C@@](C)([C@H]1CC[C@@](C)([C@@H](CC[C@@H]([C@@]2(C)CC[C@H]([C@](C)(CCC=C(C)C)O)O2)OC(=O)C)OC(=O)C)O1)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.41	Volume:	639.283 ? Van der Waals volume.
Dense:	0.93	LogP:	5.433 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.192 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.504 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	14.0
TPSA:	111.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.163	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.427	Fsp³:	0.824
MCE-18:	58.71 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.364	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.641	Promiscuous compounds:	0.324

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.716	MDCK Permeability:	-4.871
Pgp-inhibitor:	1.0	Pgp-substrate:	0.002
PAMPA:	0.321 ? 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):	0.014
20% Bioavailability (F20%):	0.935	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.804
Plasma Protein Binding (PPB):	75.198%	Volume Distribution (VD):	-0.474
Fu:	14.964% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.995
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.954	CYP1A2-substrate:	0.494
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.416	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.871
HLM stability:	0.979 ? 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):

8.129

Half-life (T1/2):

0.578

ADMET: Toxicity

hERG Blockers:	0.157	hERG Blockers (10um):	0.529
Human Hepatotoxicity (H-HT):	0.734	Drug-induced Liver Injury (DILI):	0.11
AMES Toxicity:	0.373	Rat Oral Acute Toxicity:	0.233
Maximum Recommended Daily Dose:	0.114	Skin Sensitization:	0.998
Carcinogencity:	0.288	Eye Corrosion:	0.149
Eye Irritation:	0.271	Respiratory Toxicity:	0.139
Drug-induced Neurotoxicity:	0.318	Ototoxicity:	0.702
Hematotoxicity:	0.226	Drug-induced Nephrotoxicity:	0.535
Genotoxicity:	0.265	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.054	Hek293 Cytotoxicity:	0.05
BCF:	1.062 ? 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:	4.003 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.925 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.088 ? 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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19659728]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28368118]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667820]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38163555]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13494	Prosopis kuntzei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8220	Russula sardonia	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20997	Eurycoma sp.	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20383	Stenocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12988	Blainvillea latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20997	Eurycoma sp.	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8820	Lophocereus marginatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1418	Boletinus paluster	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2084	Acinetobacter calcoaceticus	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6626	Pteris spinulosa	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11072	Geigeria schinzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6014	Goniothalamus undulatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14280	Helichrysum angustifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3576	Bersama swinnyi	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8220	Russula sardonia	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13692	Leontice kiangnanensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12026	Papaver radicatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2505	Pachycereus pringlei	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20383	Stenocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9375	Medium grandiflorum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13494	Prosopis kuntzei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13798	Cheilanthes marantae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22888	Lophiostoma vaginatispora	Species	Lophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12890	Ophryosporus charua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8640	Nemuaron humboldtii	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12577	Pinus glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12988	Blainvillea latifolia	Species	Asteraceae	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	1

Activity Type	# Activity
Others	1

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
NPT27	Others	Unspecified	n.a.	IC50	>	100.0	ug.mL-1	PMID[9873476]

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 NPC165330 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	17770
0.1-0.2	27543
0.2-0.3	4382
0.3-0.4	145
0.4-0.5	10
0.5-0.6	6
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
0.7917	Intermediate Similarity	NPC3852
0.7857	Intermediate Similarity	NPC306085
0.5439	Remote Similarity	NPC149725
0.5439	Remote Similarity	NPC304509
0.541	Remote Similarity	NPC474761
0.5345	Remote Similarity	NPC474762
0.5254	Remote Similarity	NPC47958
0.5238	Remote Similarity	NPC476004

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC165330 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6348
0.1-0.2	2723
0.2-0.3	77
0.3-0.4	2
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