NPASS Compound

Natural Product: NPC485944

Natural Product ID	NPC485944
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FGSMSNKIWGRJOM-PIHUVOOSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002748] Ibogan-type 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 105114 0 0 0 0 0 0 0 0999 V2000 4.4415 -0.6376 4.9587 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5192 0.1244 4.2155 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8279 0.8375 3.0499 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8871 1.5990 2.3027 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1213 0.8965 0.9918 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8473 0.9134 0.1619 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6151 0.4973 0.9161 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8096 -0.5045 0.1479 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1616 -1.7642 -0.2339 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4004 -2.5973 -0.0627 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8478 -2.5317 1.4187 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0403 -1.1488 1.7027 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0744 -0.1553 2.2302 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2930 -0.5726 1.3887 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3968 -1.1295 1.4142 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0715 -2.3246 -0.9264 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9239 -3.5674 -1.5135 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7179 -3.8282 -2.1305 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3012 -2.9321 -2.1795 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1072 -1.6676 -1.5634 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2318 -0.8014 -1.6505 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1928 0.6854 -1.4483 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4501 1.2674 -1.9514 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6022 2.2081 -3.0381 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7892 3.1225 -3.4503 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5062 3.3705 -2.8445 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9876 2.0384 -3.7050 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0296 1.8762 -2.7411 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.3962 3.2360 -2.3639 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1144 3.8195 -2.1660 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6333 3.2962 -1.0298 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4557 1.7730 -0.9569 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7372 1.1969 -1.5005 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7534 -0.2744 -1.6004 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7890 -1.0957 -0.8418 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2759 -1.9298 0.1418 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5181 -2.2098 0.6574 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7244 -3.1190 1.6731 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6497 -3.7885 2.2099 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3914 -3.5260 1.7105 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2041 -2.5981 0.6783 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0665 -2.2222 0.0763 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4156 -1.3174 -0.8406 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2168 1.6012 0.4545 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9929 0.9556 1.1736 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1086 2.1586 1.0588 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8482 2.0097 2.4548 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0776 -1.3436 -0.9301 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5428 -0.2632 -0.2816 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5216 -3.2289 -2.8180 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7815 -4.4397 -3.4402 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7811 1.6844 1.1556 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3742 2.0830 2.2807 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3582 2.5044 0.0837 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5590 3.6525 0.3052 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4068 -1.6601 4.5546 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6419 -0.6589 6.0390 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4505 -0.1457 4.8010 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9835 0.9132 4.8406 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3294 -0.5224 3.8432 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1724 1.5874 3.5194 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8650 1.6251 2.8291 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6143 2.6581 2.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9527 1.2581 0.4010 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9849 0.1856 -0.6770 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7698 1.9366 -0.2665 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2174 -3.6528 -0.2455 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2291 -2.2125 -0.6670 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0286 -2.9311 2.0441 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7607 -3.1232 1.4996 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2692 -0.6040 2.7958 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7269 -4.2686 -1.4728 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6068 -4.8220 -2.5975 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6374 -0.8877 -2.7397 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0800 0.8025 -0.3433 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3383 1.0815 -1.9568 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8510 0.3317 -2.5143 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1384 3.7202 -4.3185 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4581 3.3842 -1.7470 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3301 2.8407 -3.3412 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2589 4.4621 -3.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1442 2.9039 -4.3339 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8858 1.0966 -4.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8513 3.7663 -3.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9822 3.2857 -1.4410 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7088 3.8033 -0.6318 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4078 3.5099 -0.2297 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5261 1.5661 -0.7732 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7981 -0.5848 -1.2781 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7973 -0.6306 -2.6904 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3589 -1.7073 0.2617 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7080 -3.3307 2.0702 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8332 -4.4999 3.0082 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5640 -4.0611 2.1453 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1234 -2.6007 0.3227 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6810 0.9704 2.7497 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9976 2.6821 2.6965 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7393 2.4650 2.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0303 0.6091 -0.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9470 -4.8186 -4.0603 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0294 -5.2267 -2.6950 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6639 -4.3361 -4.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5696 3.4269 0.7167 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5060 4.2032 -0.6554 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1666 4.3217 0.9846 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 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 2 0 9 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 1 0 32 44 1 1 44 45 2 0 44 46 1 0 46 47 1 0 20 48 2 0 48 49 1 0 19 50 1 0 50 51 1 0 7 52 1 1 52 53 2 0 52 54 1 0 54 55 1 0 13 3 1 0 48 16 1 0 14 5 1 0 43 21 1 0 13 7 1 0 32 23 1 0 43 35 2 0 49 8 1 0 33 28 1 0 41 36 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 0 2 60 1 0 3 61 1 1 4 62 1 0 4 63 1 0 5 64 1 6 6 65 1 0 6 66 1 0 10 67 1 0 10 68 1 0 11 69 1 0 11 70 1 0 13 71 1 1 17 72 1 0 18 73 1 0 21 74 1 6 22 75 1 0 22 76 1 0 23 77 1 6 25 78 1 0 26 79 1 0 26 80 1 0 26 81 1 0 27 82 1 0 27 83 1 0 29 84 1 0 29 85 1 0 31 86 1 0 31 87 1 0 33 88 1 1 34 89 1 0 34 90 1 0 37 91 1 0 38 92 1 0 39 93 1 0 40 94 1 0 42 95 1 0 47 96 1 0 47 97 1 0 47 98 1 0 49 99 1 0 51100 1 0 51101 1 0 51102 1 0 55103 1 0 55104 1 0 55105 1 0 M END

Standard InCHIKey	FGSMSNKIWGRJOM-PIHUVOOSSA-N
Standard InCHI	InChI=1S/C44H50N4O7/c1-6-23-16-25-19-43(41(50)53-4)38-28(14-15-48(39(23)43)40(25)49)27-12-13-33(52-3)35(37(27)46-38)30-17-31-24(7-2)20-47-22-55-21-44(31,42(51)54-5)34(47)18-29-26-10-8-9-11-32(26)45-36(29)30/h7-13,23,25,30-31,34,39,45-46H,6,14-22H2,1-5H3/b24-7-/t23-,25+,30-,31+,34-,39-,43+,44-/m0/s1
SMILES	CC[C@H]1C[C@@H]2C[C@]3(c4c(CCN([C@@H]13)C2=O)c1ccc(c([C@@H]2C[C@@H]3/C(=CC)/CN5COC[C@]3([C@@H]5Cc3c5ccccc5[nH]c23)C(=O)OC)c1[nH]4)OC)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	746.37	Volume:	757.896 ? Van der Waals volume.
Dense:	0.985	LogP:	4.102 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.265 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.782 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	52.0
TPSA:	126.19 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	11.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.196	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.178	Fsp³:	0.523
MCE-18:	203.433 ? 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:	0.726	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.888 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.77 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.813

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.145	MDCK Permeability:	-5.026
Pgp-inhibitor:	0.0	Pgp-substrate:	0.975
PAMPA:	0.009 ? 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%):	0.021	30% Bioavailability (F30%):	0.5
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115	MRP1:	1.0
Plasma Protein Binding (PPB):	96.215%	Volume Distribution (VD):	0.44
Fu:	3.458% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.862
OATP1B3 inhibitor:	0.783	BCRP inhibitor:	0.572
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.998	CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.422
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.994
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.733
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.948 ? 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):

8.959

Half-life (T1/2):

0.844

ADMET: Toxicity

hERG Blockers:	0.882	hERG Blockers (10um):	0.517
Human Hepatotoxicity (H-HT):	0.95	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.951	Rat Oral Acute Toxicity:	0.994
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	0.988
Carcinogencity:	0.932	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.99	Ototoxicity:	0.951
Hematotoxicity:	0.829	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.743
A549 Cytotoxicity:	0.994	Hek293 Cytotoxicity:	0.997
BCF:	1.455 ? 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:	4.721 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.12 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.895 ? 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
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[24773071]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	stem-bark	Pahang, Malaysia	2003-JUN	PMID[25919190]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26918761]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27077800]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29319316]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30869890]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32356659]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

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	5
EC50	1

Activity Type	# Activity
Cell line	6

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
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[32356659]
NPT165	Cell line	HeLa	Homo sapiens	EC50	>	40000.0	nM	PMID[32356659]
NPT660	Cell line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[32356659]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[32356659]
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[32356659]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[32356659]

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 NPC485944 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	19555
0.1-0.2	29648
0.2-0.3	561
0.3-0.4	61
0.4-0.5	19
0.5-0.6	10
0.6-0.7	3
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
0.7054	Intermediate Similarity	NPC485908
0.6822	Remote Similarity	NPC485935
0.6774	Remote Similarity	NPC485967
0.6617	Remote Similarity	NPC485910
0.5643	Remote Similarity	NPC485917
0.5643	Remote Similarity	NPC485954
0.5556	Remote Similarity	NPC485968
0.5248	Remote Similarity	NPC488882
0.5248	Remote Similarity	NPC485918
0.5248	Remote Similarity	NPC485915
0.5211	Remote Similarity	NPC485912
0.5133	Remote Similarity	NPC485916
0.5133	Remote Similarity	NPC485932
0.5034	Remote Similarity	NPC485943

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC485944 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4344
0.1-0.2	4757
0.2-0.3	47
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