NPASS Compound

Natural Product: NPC79068

Natural Product ID	NPC79068
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	COIUWGNHAYDCDZ-RYZDBJHRSA-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:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

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 103109 0 0 0 0 0 0 0 0999 V2000 -2.3682 2.6254 1.0003 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6424 1.1260 0.9274 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0793 0.5144 2.1747 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6100 0.9549 2.2732 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1472 0.3153 1.1560 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4398 0.6616 -0.1924 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9142 0.5499 -0.2568 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3754 1.3738 -1.4671 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7908 0.9708 -1.6990 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7079 1.1235 -0.5258 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1198 0.9156 0.8179 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4552 -0.4230 1.4331 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8929 -0.7654 1.4262 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7424 -0.0708 0.3895 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4654 1.1068 1.0002 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6965 -1.0763 -0.2091 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7055 -1.9947 -0.9337 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6122 -1.0640 -1.4145 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9171 0.2794 -0.8048 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7273 0.9780 -1.7017 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6941 -0.5463 -1.1336 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7111 -0.7867 -2.4483 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8414 -0.1127 -3.0643 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1755 -0.1120 -4.2979 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5253 0.5486 -2.0936 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8544 0.3160 -0.8637 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4714 0.6695 1.1963 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3222 -0.4261 1.3511 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1680 -0.3908 2.5712 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3064 0.5697 2.5617 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5849 0.9545 1.1354 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4157 -0.3424 0.3276 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9587 -0.1973 -1.0586 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3072 -0.0674 -1.1940 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0493 -1.1842 -0.7762 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0287 -0.7928 0.2481 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2919 -1.6153 0.0993 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8718 -1.4376 -1.2690 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7956 -1.2570 -2.3215 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7134 0.1762 -2.7641 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9924 0.6256 -3.1562 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5920 -1.7890 -1.9223 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7231 -2.5087 -1.6065 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1806 -1.2619 1.1104 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5022 -1.1155 1.5241 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0326 -0.5601 0.1801 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8506 1.4213 0.9903 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1279 1.6832 3.3563 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6187 -1.7126 2.8010 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0949 3.2146 0.4134 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4750 2.9280 2.0689 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3382 2.8335 0.6317 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5513 0.8287 3.1056 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0175 -0.6105 2.0920 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5196 2.0406 2.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1845 0.5587 3.2251 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0362 -0.7970 1.2597 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0046 -0.0688 -0.9214 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0517 1.6650 -0.5176 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2056 -0.5081 -0.3748 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7748 0.9970 -2.3205 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2163 2.4368 -1.2610 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7756 -0.0383 -2.1544 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1772 1.6312 -2.5327 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0722 2.1972 -0.5663 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5746 1.6668 1.5358 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7610 -1.2054 1.0658 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1551 -0.3106 2.5219 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0194 -1.8543 1.3676 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3894 -0.4989 2.4171 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4336 0.7462 1.3833 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9299 1.4624 1.9273 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5679 1.9722 0.3591 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1689 -1.7218 0.5734 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1778 -2.5392 -1.7821 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3415 -2.8083 -0.2730 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6673 -1.5149 -1.1065 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6429 -1.0206 -2.5255 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2161 1.4256 -2.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0339 -1.3711 -3.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6013 1.3408 -0.5067 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6095 -0.1703 -0.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7119 -1.3817 1.4237 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5485 -0.1608 3.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2025 0.0338 2.9694 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8496 1.7158 0.7763 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8543 -1.1518 0.9094 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6349 -1.1332 -1.6076 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4710 0.6876 -1.5285 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2908 -1.8986 -0.3538 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2521 0.2930 0.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0265 -2.6819 0.2324 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4954 -0.5267 -1.2745 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1169 -1.8444 -3.2071 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2713 0.8618 -2.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0914 0.2930 -3.6885 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3733 1.1824 -2.4133 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2230 -3.3648 -1.6235 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0508 -1.7484 1.9430 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0309 -0.6015 2.1973 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1600 1.9312 1.7765 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8898 1.3960 4.2686 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1796 -1.6573 3.6207 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 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 0 9 10 1 0 10 11 1 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 6 16 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 5 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 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 32 46 1 0 31 47 1 0 30 48 1 0 29 49 1 0 7 2 1 0 19 10 1 0 26 21 1 0 46 28 1 0 11 2 1 0 19 14 1 0 42 35 1 0 1 50 1 0 1 51 1 0 1 52 1 0 3 53 1 0 3 54 1 0 4 55 1 0 4 56 1 0 5 57 1 1 6 58 1 0 6 59 1 0 7 60 1 6 8 61 1 0 8 62 1 0 9 63 1 0 9 64 1 0 10 65 1 1 11 66 1 1 12 67 1 0 12 68 1 0 13 69 1 0 13 70 1 0 15 71 1 0 15 72 1 0 15 73 1 0 16 74 1 1 17 75 1 0 17 76 1 0 18 77 1 0 18 78 1 0 20 79 1 0 22 80 1 0 26 81 1 0 26 82 1 0 28 83 1 1 29 84 1 1 30 85 1 1 31 86 1 6 32 87 1 1 33 88 1 0 33 89 1 0 35 90 1 1 36 91 1 1 37 92 1 1 38 93 1 1 39 94 1 6 40 95 1 0 40 96 1 0 41 97 1 0 43 98 1 0 44 99 1 0 45100 1 0 47101 1 0 48102 1 0 49103 1 0 M END

Standard InCHIKey	COIUWGNHAYDCDZ-RYZDBJHRSA-N
Standard InCHI	InChI=1S/C35H54O14/c1-33-8-5-18(47-32-30(43)28(41)26(39)23(49-32)15-46-31-29(42)27(40)25(38)22(13-36)48-31)12-17(33)3-4-21-20(33)6-9-34(2)19(7-10-35(21,34)44)16-11-24(37)45-14-16/h11,17-23,25-32,36,38-44H,3-10,12-15H2,1-2H3/t17-,18-,19+,20+,21+,22-,23-,25-,26-,27+,28+,29-,30-,31-,32-,33-,34+,35-/m0/s1
SMILES	C[C@]12CC[C@@H](C[C@@H]1CC[C@@H]1[C@H]2CC[C@]2(C)[C@H](CC[C@]12O)C1=CC(=O)OC1)O[C@@H]1[C@H]([C@@H]([C@H]([C@H](CO[C@@H]2[C@H]([C@@H]([C@H]([C@H](CO)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	698.35	Volume:	671.811 ? Van der Waals volume.
Dense:	1.04	LogP:	0.508 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.264 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.027 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	38.0
TPSA:	225.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.121	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.542	Fsp³:	0.914
MCE-18:	133.284 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.774	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.019 ? 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:	0.146	Promiscuous compounds:	0.277

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.769	MDCK Permeability:	-5.068
Pgp-inhibitor:	0.0	Pgp-substrate:	0.883
PAMPA:	0.998 ? 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):	0.895
20% Bioavailability (F20%):	0.756	30% Bioavailability (F30%):	0.978
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.53	MRP1:	0.13
Plasma Protein Binding (PPB):	70.385%	Volume Distribution (VD):	-0.4
Fu:	24.267% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.027
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.416	CYP3A4-substrate:	0.878
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.947
HLM stability:	0.001 ? 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):

0.38

Half-life (T1/2):

2.953

ADMET: Toxicity

hERG Blockers:	0.05	hERG Blockers (10um):	0.539
Human Hepatotoxicity (H-HT):	0.848	Drug-induced Liver Injury (DILI):	0.801
AMES Toxicity:	0.721	Rat Oral Acute Toxicity:	0.6
Maximum Recommended Daily Dose:	0.993	Skin Sensitization:	1.0
Carcinogencity:	0.591	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.612
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.933
Hematotoxicity:	0.279	Drug-induced Nephrotoxicity:	0.996
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.855
A549 Cytotoxicity:	0.562	Hek293 Cytotoxicity:	0.937
BCF:	0.9 ? 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:	3.213 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.488 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.853 ? 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
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252914]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19251412]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37375900]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3369	Anemone narcissiflora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2175	Hyperbaena columbica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8349	Uga sinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26375	Viburnum grandifolium	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9165	Asclepias curassavica	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 NPC79068 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	14789
0.1-0.2	28750
0.2-0.3	4668
0.3-0.4	1340
0.4-0.5	148
0.5-0.6	49
0.6-0.7	67
0.7-0.8	0
0.8-0.85	11
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC30483
1.0	High Similarity	NPC470897
0.9079	High Similarity	NPC5311
0.8837	High Similarity	NPC486144
0.8837	High Similarity	NPC486145
0.8837	High Similarity	NPC486147
0.8837	High Similarity	NPC486148
0.8621	High Similarity	NPC475590
0.8427	Intermediate Similarity	NPC475419
0.8333	Intermediate Similarity	NPC474908
0.8333	Intermediate Similarity	NPC486134
0.8333	Intermediate Similarity	NPC486141
0.8214	Intermediate Similarity	NPC236973
0.8214	Intermediate Similarity	NPC292467
0.814	Intermediate Similarity	NPC486143
0.814	Intermediate Similarity	NPC486142
0.814	Intermediate Similarity	NPC486149
0.8101	Intermediate Similarity	NPC99620
0.8065	Intermediate Similarity	NPC474423
0.7901	Intermediate Similarity	NPC77299
0.7901	Intermediate Similarity	NPC480906
0.7805	Intermediate Similarity	NPC480914
0.7802	Intermediate Similarity	NPC486136
0.7556	Intermediate Similarity	NPC486146
0.75	Intermediate Similarity	NPC479360
0.75	Intermediate Similarity	NPC479359
0.7442	Intermediate Similarity	NPC480907
0.7381	Intermediate Similarity	NPC76572
0.7381	Intermediate Similarity	NPC193382
0.7303	Intermediate Similarity	NPC480910
0.7303	Intermediate Similarity	NPC240070
0.7303	Intermediate Similarity	NPC480909
0.7292	Intermediate Similarity	NPC486150
0.7263	Intermediate Similarity	NPC120390
0.7191	Intermediate Similarity	NPC32177
0.7191	Intermediate Similarity	NPC469756
0.7191	Intermediate Similarity	NPC275901
0.7143	Intermediate Similarity	NPC486135
0.7143	Intermediate Similarity	NPC486137
0.7111	Intermediate Similarity	NPC188234
0.7083	Intermediate Similarity	NPC74259
0.7065	Intermediate Similarity	NPC232785
0.7065	Intermediate Similarity	NPC486139
0.7059	Intermediate Similarity	NPC469750
0.7041	Intermediate Similarity	NPC488945
0.7041	Intermediate Similarity	NPC488946
0.6941	Remote Similarity	NPC84987
0.6848	Remote Similarity	NPC231518
0.6848	Remote Similarity	NPC488944
0.6842	Remote Similarity	NPC479357
0.6842	Remote Similarity	NPC486131
0.6824	Remote Similarity	NPC471633
0.68	Remote Similarity	NPC488947
0.6782	Remote Similarity	NPC199428
0.6782	Remote Similarity	NPC109448
0.6782	Remote Similarity	NPC310341
0.6774	Remote Similarity	NPC125077
0.6771	Remote Similarity	NPC486128
0.6744	Remote Similarity	NPC196429
0.6667	Remote Similarity	NPC286809
0.6667	Remote Similarity	NPC610296
0.6632	Remote Similarity	NPC329986
0.6632	Remote Similarity	NPC140092
0.6596	Remote Similarity	NPC208193
0.6562	Remote Similarity	NPC486138
0.6562	Remote Similarity	NPC276838
0.65	Remote Similarity	NPC194716
0.6484	Remote Similarity	NPC72260
0.6436	Remote Similarity	NPC486133
0.6429	Remote Similarity	NPC488943
0.6429	Remote Similarity	NPC488942
0.6404	Remote Similarity	NPC84949
0.6404	Remote Similarity	NPC480562
0.6404	Remote Similarity	NPC74945
0.6404	Remote Similarity	NPC31354
0.6404	Remote Similarity	NPC69576
0.6364	Remote Similarity	NPC479358
0.6316	Remote Similarity	NPC475629
0.6292	Remote Similarity	NPC157376
0.6292	Remote Similarity	NPC142066
0.6292	Remote Similarity	NPC603972
0.6277	Remote Similarity	NPC40749
0.6264	Remote Similarity	NPC471353
0.625	Remote Similarity	NPC99728
0.625	Remote Similarity	NPC87250
0.625	Remote Similarity	NPC244402
0.625	Remote Similarity	NPC50305
0.6211	Remote Similarity	NPC32793
0.6211	Remote Similarity	NPC479353
0.6211	Remote Similarity	NPC116075
0.6211	Remote Similarity	NPC479354
0.6211	Remote Similarity	NPC486130
0.6186	Remote Similarity	NPC469749
0.6162	Remote Similarity	NPC475219
0.6146	Remote Similarity	NPC488941
0.6146	Remote Similarity	NPC488940
0.6146	Remote Similarity	NPC486127
0.6132	Remote Similarity	NPC486152
0.6111	Remote Similarity	NPC17896
0.6111	Remote Similarity	NPC469755
0.6111	Remote Similarity	NPC284406
0.6111	Remote Similarity	NPC197707
0.6111	Remote Similarity	NPC251866
0.6111	Remote Similarity	NPC480915
0.61	Remote Similarity	NPC488938
0.61	Remote Similarity	NPC488937
0.6087	Remote Similarity	NPC484202
0.6087	Remote Similarity	NPC93883
0.6087	Remote Similarity	NPC305574
0.6042	Remote Similarity	NPC475556
0.6042	Remote Similarity	NPC311706
0.6019	Remote Similarity	NPC117445
0.6019	Remote Similarity	NPC308262
0.5918	Remote Similarity	NPC55532
0.5914	Remote Similarity	NPC179412
0.5914	Remote Similarity	NPC471356
0.587	Remote Similarity	NPC243196
0.5842	Remote Similarity	NPC486132
0.5806	Remote Similarity	NPC250556
0.58	Remote Similarity	NPC146857
0.58	Remote Similarity	NPC247190
0.5778	Remote Similarity	NPC158344
0.5745	Remote Similarity	NPC483822
0.5686	Remote Similarity	NPC476221
0.5686	Remote Similarity	NPC477709
0.5657	Remote Similarity	NPC264336
0.5652	Remote Similarity	NPC219085
0.5644	Remote Similarity	NPC488939
0.5638	Remote Similarity	NPC146456
0.5591	Remote Similarity	NPC479356
0.5591	Remote Similarity	NPC479355
0.5566	Remote Similarity	NPC486140
0.5543	Remote Similarity	NPC473852
0.5542	Remote Similarity	NPC268829
0.5542	Remote Similarity	NPC295110
0.5484	Remote Similarity	NPC309034
0.5455	Remote Similarity	NPC27363
0.5446	Remote Similarity	NPC59288
0.5421	Remote Similarity	NPC329675
0.5408	Remote Similarity	NPC173555
0.5361	Remote Similarity	NPC193893
0.5312	Remote Similarity	NPC77319
0.5312	Remote Similarity	NPC471351
0.5312	Remote Similarity	NPC471355
0.5263	Remote Similarity	NPC99080
0.5253	Remote Similarity	NPC5883
0.5233	Remote Similarity	NPC222875
0.5233	Remote Similarity	NPC25177
0.5229	Remote Similarity	NPC329784
0.5208	Remote Similarity	NPC604978
0.5204	Remote Similarity	NPC471354
0.5204	Remote Similarity	NPC27507
0.5116	Remote Similarity	NPC480913
0.5106	Remote Similarity	NPC474418
0.5102	Remote Similarity	NPC9499
0.5102	Remote Similarity	NPC471360
0.5102	Remote Similarity	NPC469751
0.5102	Remote Similarity	NPC471361
0.5102	Remote Similarity	NPC86159
0.5102	Remote Similarity	NPC469752
0.5102	Remote Similarity	NPC469754
0.5102	Remote Similarity	NPC70542

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC79068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6093
0.1-0.2	2920
0.2-0.3	114
0.3-0.4	7
0.4-0.5	6
0.5-0.6	5
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	Drug ID	Developmental Stage
0.6848	Remote Similarity	NPD8033	Approved
0.6484	Remote Similarity	NPD8294	Phase 4
0.6111	Remote Similarity	NPD7319	Approved
0.5918	Remote Similarity	NPD8377	Phase 4
0.5806	Remote Similarity	NPD7507	Pre-clinical
0.5408	Remote Similarity	NPD8296	Phase 4
0.5312	Remote Similarity	NPD8335	Phase 4
0.5258	Remote Similarity	NPD8380	Approved

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