NPASS Compound

Natural Product: NPC60174

Natural Product ID	NPC60174
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XFSBVAOIAHNAPC-PHLDZCGOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	16210989
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003788] Aconitane-type diterpenoid alkaloids

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 93 99 0 0 0 0 0 0 0 0999 V2000 -4.5315 -2.2339 -1.8222 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5221 -1.1566 -2.1879 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9204 -0.6862 -0.9653 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8226 0.0241 -0.1448 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2495 1.0322 0.7817 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8642 0.9616 2.1787 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2688 1.2305 2.0622 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7980 1.1638 3.3516 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7090 2.4381 0.2993 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6712 3.1427 -0.4952 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0730 2.1158 -1.4356 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3004 1.1283 -0.6411 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1250 1.4964 -0.6228 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8016 1.5117 -1.9597 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1895 0.9288 -1.7502 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3721 1.0364 -0.2492 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0002 0.5726 0.1930 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7180 -0.8735 -0.0970 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7596 -1.0507 -0.0650 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2807 -0.3805 1.2272 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7788 0.9843 0.8250 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2133 -1.2533 1.7219 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8434 -1.8503 2.9391 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5678 -0.3012 -1.0659 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3852 -1.4257 -1.3140 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2700 -0.5147 -2.0893 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6415 -0.8484 -1.9547 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2481 -1.1378 -3.1501 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4481 -1.9804 -2.2083 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2432 -1.5994 1.0073 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1703 -2.9879 1.0728 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6393 -3.6631 0.1689 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7285 -3.7548 2.2380 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4350 0.3073 0.2605 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4556 0.9470 0.9771 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3333 2.1973 1.1167 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5894 0.2176 1.5275 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7582 -1.1408 1.4049 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8666 -1.7892 1.9496 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8181 -1.0917 2.6217 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6632 0.2708 2.7533 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5583 0.9227 2.2112 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1699 1.6078 -2.4526 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2960 2.7847 -2.3418 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7616 2.7463 -3.6490 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9144 2.3181 -0.3659 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5215 -1.8129 -1.5979 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6509 -2.8659 -2.7347 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1097 -2.8768 -1.0368 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7363 -1.6546 -2.7868 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9746 -0.3686 -2.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3615 -0.7361 0.4982 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6139 0.4793 -0.7692 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4789 1.7695 2.8262 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8623 -0.0394 2.6260 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8857 1.3703 3.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6253 0.1858 3.8184 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3278 1.9987 3.9446 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9109 3.0822 1.1981 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1869 3.8923 -1.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8814 3.6138 0.1075 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 1.6703 -2.0091 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2196 2.5137 -0.1635 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3032 0.9488 -2.7419 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0043 2.5466 -2.3513 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4196 2.1226 -0.0294 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9206 0.8455 1.2442 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0854 -2.1087 -0.1115 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4576 -0.3576 1.9795 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3293 1.7932 1.4392 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9245 -2.4358 2.8910 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7527 -1.0777 3.7426 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6968 -2.5168 3.2370 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2556 -0.4179 -2.1222 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0498 -2.3108 -1.0597 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0779 -0.5923 -3.2014 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3139 -1.3811 -2.9088 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1875 -0.2443 -3.8043 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8514 -2.0611 -3.6473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7201 -2.8587 -2.5558 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1281 -3.1047 3.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9236 -4.4017 2.6956 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4630 -4.4678 1.8105 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0088 -1.7025 0.8727 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0029 -2.8640 1.8539 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6816 -1.6174 3.0420 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4283 0.8122 3.2908 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4916 1.9966 2.3478 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0237 1.6250 -1.9624 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7676 3.1850 -3.7691 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0834 3.4408 -4.2259 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6328 1.7622 -4.1309 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6484 2.8540 0.0122 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 1 6 7 1 0 7 8 1 0 5 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 19 24 1 0 18 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 25 29 1 0 18 30 1 1 30 31 1 0 31 32 2 0 31 33 1 0 16 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 15 43 1 6 11 44 1 0 44 45 1 0 9 46 1 0 24 3 1 0 42 37 1 0 21 5 1 0 21 12 1 0 24 12 1 0 17 13 1 0 26 15 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 0 2 51 1 0 4 52 1 0 4 53 1 0 6 54 1 0 6 55 1 0 8 56 1 0 8 57 1 0 8 58 1 0 9 59 1 1 10 60 1 0 10 61 1 0 11 62 1 6 13 63 1 1 14 64 1 0 14 65 1 0 16 66 1 6 17 67 1 1 19 68 1 0 20 69 1 1 21 70 1 0 23 71 1 0 23 72 1 0 23 73 1 0 24 74 1 6 25 75 1 1 26 76 1 6 28 77 1 0 28 78 1 0 28 79 1 0 29 80 1 0 33 81 1 0 33 82 1 0 33 83 1 0 38 84 1 0 39 85 1 0 40 86 1 0 41 87 1 0 42 88 1 0 43 89 1 0 45 90 1 0 45 91 1 0 45 92 1 0 46 93 1 0 M END

Standard InCHIKey	XFSBVAOIAHNAPC-PHLDZCGOSA-N
Standard InCHI	InChI=1S/C34H47NO11/c1-7-35-15-31(16-41-3)20(37)13-21(42-4)33-19-14-32(40)28(45-30(39)18-11-9-8-10-12-18)22(19)34(46-17(2)36,27(38)29(32)44-6)23(26(33)35)24(43-5)25(31)33/h8-12,19-29,37-38,40H,7,13-16H2,1-6H3/t19-,20-,21-,22-,23?,24+,25?,26-,27+,28-,29+,31+,32-,33?,34-/m1/s1
SMILES	CCN1C[C@]2(COC)[C@@H](C[C@H](C34[C@@H]5C[C@]6([C@@H]([C@@H]5[C@@](C([C@@H](C23)OC)[C@@H]14)([C@H]([C@@H]6OC)O)OC(=O)C)OC(=O)c1ccccc1)O)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	645.31	Volume:	631.232 ? Van der Waals volume.
Dense:	1.022	LogP:	1.307 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.781 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.719 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	32.0
TPSA:	153.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	3.0	Rings:	7.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.323	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.257	Fsp³:	0.765
MCE-18:	220.8 ? 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:	0.198	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.002	Promiscuous compounds:	0.047

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.527	MDCK Permeability:	-5.18
Pgp-inhibitor:	0.839	Pgp-substrate:	0.99
PAMPA:	0.056 ? 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):	0.002
20% Bioavailability (F20%):	0.139	30% Bioavailability (F30%):	0.315
50% Bioavailability (F50%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064	MRP1:	0.988
Plasma Protein Binding (PPB):	43.671%	Volume Distribution (VD):	0.026
Fu:	58.779% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.958	BCRP inhibitor:	0.025
BSEP inhibitor:	0.92

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.016
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.259	CYP3A4-substrate:	0.004
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
HLM stability:	0.997 ? 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):

8.046

Half-life (T1/2):

1.953

ADMET: Toxicity

hERG Blockers:	0.057	hERG Blockers (10um):	0.495
Human Hepatotoxicity (H-HT):	0.202	Drug-induced Liver Injury (DILI):	0.14
AMES Toxicity:	0.487	Rat Oral Acute Toxicity:	0.257
Maximum Recommended Daily Dose:	0.355	Skin Sensitization:	0.951
Carcinogencity:	0.414	Eye Corrosion:	0.002
Eye Irritation:	0.227	Respiratory Toxicity:	0.554
Drug-induced Neurotoxicity:	0.286	Ototoxicity:	0.815
Hematotoxicity:	0.301	Drug-induced Nephrotoxicity:	0.845
Genotoxicity:	0.126	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.136	Hek293 Cytotoxicity:	0.301
BCF:	0.393 ? 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:	3.147 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.724 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.72 ? 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
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	tuber	n.a.	PMID[12913245]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1293938]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16181762]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[18044843]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22223386]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	Lateral roots	n.a.	n.a.	PMID[22607495]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22628040]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22907155]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[23225552]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23707213]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[23707213]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24170571]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24170571]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24190290]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24190290]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24793215]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[27761113]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[300080]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	Europe PMC[300080]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30892884]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14688	Aconitum triphyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4893	Aconitum ciliare	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	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 NPC60174 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	12064
0.1-0.2	35983
0.2-0.3	1519
0.3-0.4	260
0.4-0.5	3
0.5-0.6	4
0.6-0.7	7
0.7-0.8	0
0.8-0.85	5
0.85-0.9	2
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC298772
1.0	High Similarity	NPC108276
1.0	High Similarity	NPC163578
0.9136	High Similarity	NPC478540
0.9024	High Similarity	NPC184195
0.9024	High Similarity	NPC205
0.8837	High Similarity	NPC94687
0.8506	High Similarity	NPC478538
0.8118	Intermediate Similarity	NPC488583
0.8118	Intermediate Similarity	NPC478535
0.8095	Intermediate Similarity	NPC166521
0.8068	Intermediate Similarity	NPC476495
0.8046	Intermediate Similarity	NPC172769
0.7667	Intermediate Similarity	NPC478539
0.7333	Intermediate Similarity	NPC488604
0.7333	Intermediate Similarity	NPC281470
0.7303	Intermediate Similarity	NPC478541
0.7128	Intermediate Similarity	NPC476496
0.7053	Intermediate Similarity	NPC106840
0.6848	Remote Similarity	NPC124690
0.6842	Remote Similarity	NPC478537
0.6735	Remote Similarity	NPC479698
0.6559	Remote Similarity	NPC478534
0.6458	Remote Similarity	NPC478536
0.617	Remote Similarity	NPC478545
0.6042	Remote Similarity	NPC488589
0.5918	Remote Similarity	NPC478533
0.5758	Remote Similarity	NPC40539
0.5588	Remote Similarity	NPC249360
0.5534	Remote Similarity	NPC326895

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC60174 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3122
0.1-0.2	5879
0.2-0.3	142
0.3-0.4	7
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