NPASS Compound

Natural Product: NPC605101

Natural Product ID	NPC605101
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HKMBLJVHVBJAIH-OVKYLHECSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL68350
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 111113 0 0 0 0 0 0 0 0999 V2000 -11.8853 -0.4437 3.2223 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9377 -0.4109 1.7304 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2407 0.8224 1.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3758 0.7157 -0.3435 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7535 1.8335 -1.1134 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2755 1.9474 -0.8627 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5722 0.6486 -1.2718 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1162 0.8354 -0.9931 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2852 -0.3844 -1.3425 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3747 -0.7553 -2.7961 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5573 -1.9687 -3.0689 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9837 -3.0686 -2.3149 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0737 -1.7917 -3.0128 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5803 -0.5196 -3.6717 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1484 -0.4965 -3.1001 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3208 -1.1540 -1.7739 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4920 -2.3672 -1.5346 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8049 -2.8866 -0.2803 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0702 -2.3306 -1.8572 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 -1.3686 -1.2414 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9378 -1.4390 0.2673 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3044 -1.1664 0.8528 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9731 -0.4371 0.7978 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3269 -0.9353 0.3585 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0086 -1.2519 1.6809 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2272 -0.4027 2.6358 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5779 1.0614 2.5991 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0407 1.3201 2.9656 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3464 2.7785 2.9144 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2003 3.5015 1.6626 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0481 3.4400 0.4953 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4680 2.2128 -0.1846 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5420 1.3814 0.5063 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8206 0.1258 -0.2279 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2808 0.4041 -1.5361 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7077 -0.8188 0.4807 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0733 -0.3710 0.8016 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1448 -0.9773 0.2557 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3728 -0.3412 0.7389 C 0 0 2 0 0 0 0 0 0 0 0 0 13.2184 -1.4520 1.3695 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9816 0.6033 1.6603 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5870 0.6342 1.6977 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9344 1.4281 2.4179 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9402 -0.5763 2.1851 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6669 -1.6044 -1.7188 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.9751 0.5398 3.7069 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7699 -1.0504 3.5736 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9936 -0.9841 3.6012 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3953 -1.3111 1.3281 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9891 -0.3794 1.3546 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1726 0.7446 1.4301 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7131 1.7408 1.5590 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4685 0.6895 -0.6101 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9944 -0.2851 -0.6469 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8884 1.6139 -2.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2247 2.7807 -0.8025 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8543 2.7804 -1.4352 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1198 2.1105 0.2218 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7154 0.4720 -2.3619 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9613 -0.1995 -0.6978 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9883 0.9826 0.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7518 1.6948 -1.5785 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6736 -1.2692 -0.7647 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2733 -0.1731 -0.9758 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4574 -0.9865 -2.9906 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1343 0.0951 -3.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7708 -2.2933 -4.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4922 -3.0381 -1.4554 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5387 -2.6315 -3.5230 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5542 -0.5680 -4.7591 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1147 0.3675 -3.2700 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5461 -1.0941 -3.7947 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8689 0.5631 -3.0507 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2591 -0.4181 -0.9193 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9646 -3.1562 -2.2409 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6269 -3.8713 -0.3009 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0717 -2.2687 -2.9848 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3474 -3.3681 -1.6438 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8902 -1.4933 -1.6285 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6183 -0.2971 -1.4756 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2452 -2.4434 0.6240 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2969 -1.4387 1.7992 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7608 0.5874 0.4532 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2741 -1.8464 -0.2787 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9127 -0.1813 -0.1739 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0822 -1.0876 1.6500 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7365 -2.3115 1.9077 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2634 -0.8041 3.6807 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9051 1.5562 3.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3304 1.4715 1.6121 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6714 0.6156 2.4817 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 1.0385 4.0788 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4120 2.9494 3.3076 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7216 3.2574 3.7255 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1612 4.6322 1.9776 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0997 3.4129 1.2819 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5694 4.0898 -0.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9837 4.1051 0.6830 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5679 1.5250 -0.2241 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7503 2.3810 -1.2550 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4678 1.2648 1.5573 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4806 2.0635 0.3242 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8288 -0.4297 -0.3876 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2784 0.2876 -1.5500 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7154 -1.8381 -0.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2232 -1.0068 1.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0767 -1.8269 -0.4504 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9804 0.0785 -0.1041 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0432 -1.0392 1.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6632 -2.0175 0.5322 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5427 -2.1223 1.9279 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 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 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 34 36 1 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 42 43 2 0 26 44 1 0 16 45 1 0 45 13 1 0 44 23 1 0 42 37 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 6 57 1 0 6 58 1 0 7 59 1 0 7 60 1 0 8 61 1 0 8 62 1 0 9 63 1 0 9 64 1 0 10 65 1 0 10 66 1 0 11 67 1 6 12 68 1 0 13 69 1 6 14 70 1 0 14 71 1 0 15 72 1 0 15 73 1 0 16 74 1 1 17 75 1 6 18 76 1 0 19 77 1 0 19 78 1 0 20 79 1 0 20 80 1 0 21 81 1 6 22 82 1 0 23 83 1 1 24 84 1 0 24 85 1 0 25 86 1 0 25 87 1 0 26 88 1 1 27 89 1 0 27 90 1 0 28 91 1 0 28 92 1 0 29 93 1 0 29 94 1 0 30 95 1 0 30 96 1 0 31 97 1 0 31 98 1 0 32 99 1 0 32100 1 0 33101 1 0 33102 1 0 34103 1 6 35104 1 0 36105 1 0 36106 1 0 38107 1 0 39108 1 6 40109 1 0 40110 1 0 40111 1 0 M END

Standard InCHIKey	HKMBLJVHVBJAIH-OVKYLHECSA-N
Standard InCHI	InChI=1S/C37H66O8/c1-3-4-5-6-7-8-12-15-18-31(39)35-23-24-36(45-35)33(41)21-20-32(40)34-22-19-30(44-34)17-14-11-9-10-13-16-29(38)26-28-25-27(2)43-37(28)42/h25,27,29-36,38-41H,3-24,26H2,1-2H3/t27-,29+,30+,31-,32-,33+,34-,35+,36+/m0/s1
SMILES	CCCCCCCCCC[C@H](O)[C@H]1CC[C@H]([C@H](O)CC[C@H](O)[C@@H]2CC[C@@H](CCCCCCC[C@@H](O)CC3=C[C@H](C)OC3=O)O2)O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.48	Volume:	687.887 ? Van der Waals volume.
Dense:	0.928	LogP:	4.386 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.461 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.53 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	25.0	Rigid Bonds:	16.0
TPSA:	125.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.063	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.999	Fsp³:	0.919
MCE-18:	45.07 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.901	Fluc inhibitor:	0.028 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.066 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.587	Promiscuous compounds:	0.35

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.193	MDCK Permeability:	-4.866
Pgp-inhibitor:	0.001	Pgp-substrate:	0.969
PAMPA:	0.294 ? 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):	0.001
20% Bioavailability (F20%):	0.973	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.93
Plasma Protein Binding (PPB):	95.918%	Volume Distribution (VD):	0.433
Fu:	3.691% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.95
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.658
BSEP inhibitor:	0.506

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.668	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.979
HLM stability:	0.006 ? 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):

5.489

Half-life (T1/2):

1.057

ADMET: Toxicity

hERG Blockers:	0.516	hERG Blockers (10um):	0.77
Human Hepatotoxicity (H-HT):	0.696	Drug-induced Liver Injury (DILI):	0.436
AMES Toxicity:	0.532	Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.942	Skin Sensitization:	1.0
Carcinogencity:	0.416	Eye Corrosion:	0.018
Eye Irritation:	0.655	Respiratory Toxicity:	0.97
Drug-induced Neurotoxicity:	0.161	Ototoxicity:	0.676
Hematotoxicity:	0.254	Drug-induced Nephrotoxicity:	0.926
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.143
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.586
BCF:	1.358 ? 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:	5.122 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.233 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.308 ? 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
NPO15739	Rollinia mucosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654411]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11325235]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO15739	Rollinia mucosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608866]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[14575439]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO15739	Rollinia mucosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778247]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO15739	Rollinia mucosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9556	Annona atemoya	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO48341	Annona salzmanii	Genus	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO60578	Eurytides marcellus	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15739	Rollinia mucosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9556	Annona atemoya	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26361	Annona cherimolia	Species	Annonaceae	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
TGI	1
Ratio	2
ED50	4
Inhibition	1
Activity	1
Ki	1

Activity Type	# Activity
Cell line	6
Unchecked	1
Organism	3
Non-molecular	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
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	IC50	=	9800.0	ug.mL-1	PMID[9207950]
NPT179	Cell line	A2780	Homo sapiens	TGI	=	75.0	%	PMID[18598079]
NPT81	Cell line	A549	Homo sapiens	ED50	=	2.34	10'-7 ug/ml	PMID[2199608]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	2.34	ug ml-1	PMID[2199608]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	8.8	10'-6 ug/ml	PMID[2199608]
NPT5400	Cell line	X5563	Mus musculus	Activity	=	67.0	%	PMID[10096871]
NPT28438	Unchecked	Unchecked	n.a.	Ki	=	17660.0	nM	PMID[21550257]
NPT2802	Organism	Blattella germanica	Blattella germanica	Ratio	=	0.9	n.a.	PMID[10096871]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	ug ml-1	PMID[2199608]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	63.0	%	PMID[2199608]
NPT2802	Organism	Blattella germanica	Blattella germanica	Ratio	=	1.8	n.a.	PMID[10096871]

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
-	Aedes aegypti	LC50	=	0.1	ug.mL-1	PMID[10096871]
-	Artemia	LC50	=	0.154	ppm	PMID[2199608]
-	Blattella germanica	LT50	=	6.3	ppm	PMID[10096871]
-	Blattella germanica	LT50	=	10.3	ppm	PMID[10096871]
-	Blattella germanica	LT50	=	5.8	ppm	PMID[10096871]
-	Blattella germanica	LT50	=	7.2	ppm	PMID[10096871]

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 NPC605101 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	16980
0.1-0.2	30026
0.2-0.3	2517
0.3-0.4	102
0.4-0.5	21
0.5-0.6	31
0.6-0.7	60
0.7-0.8	0
0.8-0.85	36
0.85-0.9	9
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC20621
1.0	High Similarity	NPC318963
0.898	High Similarity	NPC473478
0.898	High Similarity	NPC473651
0.898	High Similarity	NPC66346
0.88	High Similarity	NPC231096
0.88	High Similarity	NPC475581
0.88	High Similarity	NPC283085
0.88	High Similarity	NPC62118
0.88	High Similarity	NPC107717
0.88	High Similarity	NPC488252
0.8478	Intermediate Similarity	NPC606043
0.8431	Intermediate Similarity	NPC169511
0.8431	Intermediate Similarity	NPC287164
0.8431	Intermediate Similarity	NPC234077
0.8431	Intermediate Similarity	NPC132496
0.8333	Intermediate Similarity	NPC232555
0.8333	Intermediate Similarity	NPC171174
0.8333	Intermediate Similarity	NPC114694
0.8333	Intermediate Similarity	NPC485248
0.8333	Intermediate Similarity	NPC142117
0.8333	Intermediate Similarity	NPC480249
0.8333	Intermediate Similarity	NPC485249
0.8333	Intermediate Similarity	NPC240695
0.8298	Intermediate Similarity	NPC107986
0.8298	Intermediate Similarity	NPC223871
0.8298	Intermediate Similarity	NPC231009
0.8298	Intermediate Similarity	NPC103284
0.8298	Intermediate Similarity	NPC110710
0.8298	Intermediate Similarity	NPC1083
0.8298	Intermediate Similarity	NPC82795
0.8298	Intermediate Similarity	NPC286338
0.8298	Intermediate Similarity	NPC603931
0.8298	Intermediate Similarity	NPC604237
0.8163	Intermediate Similarity	NPC488632
0.8125	Intermediate Similarity	NPC488253
0.8125	Intermediate Similarity	NPC473669
0.8125	Intermediate Similarity	NPC488251
0.8077	Intermediate Similarity	NPC258068
0.8077	Intermediate Similarity	NPC476583
0.8077	Intermediate Similarity	NPC606740
0.8077	Intermediate Similarity	NPC608614
0.8	Intermediate Similarity	NPC280621
0.8	Intermediate Similarity	NPC48338
0.8	Intermediate Similarity	NPC241360
0.8	Intermediate Similarity	NPC293136
0.8	Intermediate Similarity	NPC488628
0.7963	Intermediate Similarity	NPC91067
0.7963	Intermediate Similarity	NPC480081
0.7959	Intermediate Similarity	NPC182383
0.78	Intermediate Similarity	NPC134865
0.78	Intermediate Similarity	NPC103523
0.78	Intermediate Similarity	NPC488627
0.78	Intermediate Similarity	NPC47937
0.78	Intermediate Similarity	NPC488631
0.7636	Intermediate Similarity	NPC488630
0.7636	Intermediate Similarity	NPC488625
0.7636	Intermediate Similarity	NPC488626
0.76	Intermediate Similarity	NPC81045
0.76	Intermediate Similarity	NPC39754
0.76	Intermediate Similarity	NPC171135
0.76	Intermediate Similarity	NPC61257
0.76	Intermediate Similarity	NPC320569
0.76	Intermediate Similarity	NPC133730
0.76	Intermediate Similarity	NPC191929
0.76	Intermediate Similarity	NPC100454
0.76	Intermediate Similarity	NPC242364
0.76	Intermediate Similarity	NPC172821
0.76	Intermediate Similarity	NPC274446
0.76	Intermediate Similarity	NPC485251
0.76	Intermediate Similarity	NPC151403
0.76	Intermediate Similarity	NPC261952
0.76	Intermediate Similarity	NPC605171
0.7593	Intermediate Similarity	NPC233551
0.7593	Intermediate Similarity	NPC40376
0.7593	Intermediate Similarity	NPC21208
0.75	Intermediate Similarity	NPC178215
0.75	Intermediate Similarity	NPC42598
0.75	Intermediate Similarity	NPC473687
0.75	Intermediate Similarity	NPC204686
0.75	Intermediate Similarity	NPC219498
0.75	Intermediate Similarity	NPC308412
0.75	Intermediate Similarity	NPC134885
0.75	Intermediate Similarity	NPC488247
0.75	Intermediate Similarity	NPC210218
0.75	Intermediate Similarity	NPC488248
0.7451	Intermediate Similarity	NPC93794
0.7451	Intermediate Similarity	NPC473504
0.7451	Intermediate Similarity	NPC81778
0.7451	Intermediate Similarity	NPC40066
0.7414	Intermediate Similarity	NPC482766
0.7414	Intermediate Similarity	NPC279267
0.7368	Intermediate Similarity	NPC473663
0.7368	Intermediate Similarity	NPC473723
0.7368	Intermediate Similarity	NPC475173
0.7358	Intermediate Similarity	NPC488250
0.7358	Intermediate Similarity	NPC602738
0.7273	Intermediate Similarity	NPC488623
0.7273	Intermediate Similarity	NPC488624
0.7273	Intermediate Similarity	NPC488629
0.7222	Intermediate Similarity	NPC69082
0.7222	Intermediate Similarity	NPC488249
0.717	Intermediate Similarity	NPC65930
0.7115	Intermediate Similarity	NPC477011
0.7091	Intermediate Similarity	NPC130359
0.7091	Intermediate Similarity	NPC14901
0.7037	Intermediate Similarity	NPC329615
0.7037	Intermediate Similarity	NPC134807
0.6923	Remote Similarity	NPC156804
0.6863	Remote Similarity	NPC100921
0.6863	Remote Similarity	NPC475159
0.6863	Remote Similarity	NPC131002
0.6863	Remote Similarity	NPC473780
0.6863	Remote Similarity	NPC477018
0.6863	Remote Similarity	NPC604521
0.6809	Remote Similarity	NPC608138
0.68	Remote Similarity	NPC112685
0.6667	Remote Similarity	NPC320458
0.6667	Remote Similarity	NPC477014
0.6667	Remote Similarity	NPC477013
0.6607	Remote Similarity	NPC20339
0.66	Remote Similarity	NPC73310
0.66	Remote Similarity	NPC473529
0.66	Remote Similarity	NPC180363
0.66	Remote Similarity	NPC94875
0.66	Remote Similarity	NPC11332
0.66	Remote Similarity	NPC145914
0.66	Remote Similarity	NPC601174
0.66	Remote Similarity	NPC601403
0.66	Remote Similarity	NPC603568
0.66	Remote Similarity	NPC604330
0.66	Remote Similarity	NPC608300
0.66	Remote Similarity	NPC611200
0.66	Remote Similarity	NPC611571
0.6552	Remote Similarity	NPC239517
0.6481	Remote Similarity	NPC163093
0.6429	Remote Similarity	NPC329838
0.6379	Remote Similarity	NPC480082
0.6333	Remote Similarity	NPC253801
0.625	Remote Similarity	NPC132940
0.6226	Remote Similarity	NPC329829
0.6207	Remote Similarity	NPC473995
0.6182	Remote Similarity	NPC473649
0.6182	Remote Similarity	NPC473156
0.6182	Remote Similarity	NPC154097
0.6182	Remote Similarity	NPC159750
0.6182	Remote Similarity	NPC73248
0.6182	Remote Similarity	NPC282815
0.6182	Remote Similarity	NPC470401
0.6182	Remote Similarity	NPC600956
0.6182	Remote Similarity	NPC610454
0.6167	Remote Similarity	NPC473520
0.6167	Remote Similarity	NPC322529
0.614	Remote Similarity	NPC309211
0.614	Remote Similarity	NPC20533
0.614	Remote Similarity	NPC477010
0.6071	Remote Similarity	NPC473671
0.6071	Remote Similarity	NPC475268
0.6071	Remote Similarity	NPC470400
0.6071	Remote Similarity	NPC77871
0.6071	Remote Similarity	NPC9678
0.6071	Remote Similarity	NPC319036
0.6071	Remote Similarity	NPC475616
0.6071	Remote Similarity	NPC604764
0.6071	Remote Similarity	NPC605867
0.6034	Remote Similarity	NPC473707
0.6032	Remote Similarity	NPC477017
0.6032	Remote Similarity	NPC477016
0.5965	Remote Similarity	NPC473904
0.5926	Remote Similarity	NPC25764
0.5926	Remote Similarity	NPC235809
0.5926	Remote Similarity	NPC39279
0.5926	Remote Similarity	NPC39167
0.5926	Remote Similarity	NPC292809
0.5926	Remote Similarity	NPC202055
0.5926	Remote Similarity	NPC606804
0.5926	Remote Similarity	NPC607425
0.5926	Remote Similarity	NPC608574
0.5893	Remote Similarity	NPC144415
0.5893	Remote Similarity	NPC607439
0.5893	Remote Similarity	NPC608157
0.5806	Remote Similarity	NPC477015
0.5789	Remote Similarity	NPC480079
0.5763	Remote Similarity	NPC139418
0.569	Remote Similarity	NPC480251
0.569	Remote Similarity	NPC480250
0.5667	Remote Similarity	NPC120398
0.5667	Remote Similarity	NPC471567
0.5614	Remote Similarity	NPC482767
0.5614	Remote Similarity	NPC488246
0.5614	Remote Similarity	NPC475260
0.5614	Remote Similarity	NPC488621
0.5614	Remote Similarity	NPC473775
0.5614	Remote Similarity	NPC488622
0.5614	Remote Similarity	NPC480080
0.5614	Remote Similarity	NPC600524
0.5614	Remote Similarity	NPC608355
0.5574	Remote Similarity	NPC89001
0.5517	Remote Similarity	NPC219652

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC605101 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6454
0.1-0.2	2642
0.2-0.3	54
0.3-0.4	0
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