NPASS Compound

Natural Product: NPC328571

Natural Product ID	NPC328571
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LNTOLDCVMUNKRU-XCBLAXHTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5321733
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes 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 121126 0 0 0 0 0 0 0 0999 V2000 10.1101 -1.6140 2.9924 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3022 -1.6333 1.7377 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5749 -2.9052 1.4519 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5790 -4.0285 1.3419 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5779 -3.2705 2.5288 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5317 -2.2034 2.7137 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7132 -1.9348 1.5255 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7900 -2.7596 0.5590 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8522 -0.8184 1.3902 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0376 -0.5386 0.2198 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6902 0.5080 -0.6293 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1064 1.6827 -0.0572 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7096 2.6344 -0.8373 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9187 2.4463 -2.2061 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4868 1.2555 -2.7356 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8763 0.2776 -1.9819 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6444 -0.1193 0.5955 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8401 0.3968 -0.5406 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3037 1.0066 -1.5241 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4345 0.2269 -0.5806 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3398 0.7233 -1.6630 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2272 -0.2676 -2.3049 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6918 0.1467 -2.5100 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4151 -0.3372 -1.3241 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8889 -0.0572 -1.2044 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2902 0.9970 -0.2508 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7630 0.5215 1.0992 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9588 -0.9177 1.2980 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4206 -1.6192 0.0959 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6946 -1.3334 -1.1188 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0872 -1.2128 -1.6699 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6798 -1.3197 -0.4051 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9180 -2.3531 -1.7297 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2699 -3.6509 -1.9022 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3798 -4.0468 -1.5115 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3516 -4.6135 -2.5497 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8342 0.8978 2.1140 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3231 2.0719 0.0099 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7549 2.7397 0.9364 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0214 2.7497 -0.3395 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3204 2.1234 -1.4146 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0771 1.9180 -1.0622 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4417 2.8335 -0.1138 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6780 1.6076 -2.7944 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8924 2.2994 -3.2398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5951 1.9241 -3.8027 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4130 4.0594 -0.7375 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2013 5.2098 -0.0431 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6039 5.1516 1.0687 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6785 6.4959 -0.6144 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5146 1.7687 -0.8190 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8005 -0.1558 -0.0600 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3588 -1.1936 0.7372 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5195 -2.3667 0.3112 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 -1.0433 2.0388 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2910 -2.1517 2.7539 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6828 -2.0626 3.9778 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4628 -0.8433 4.5643 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8761 0.2781 3.8766 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4947 0.1794 2.6317 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1336 -0.5342 -3.6391 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9179 -1.0495 1.3110 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2614 -0.5320 3.2884 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7187 -2.2016 3.8279 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1482 -1.9909 2.8219 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5461 -0.8112 1.7541 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9686 -1.4036 0.8831 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1029 -2.8014 0.4505 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5211 -4.7307 2.2222 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6286 -3.6173 1.4147 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4549 -4.6426 0.4318 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1227 -3.3796 3.4784 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0849 -4.2308 2.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8269 -2.6237 3.4933 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9506 -1.2803 3.1975 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8328 -0.1633 2.2290 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9971 -1.4407 -0.3928 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9516 1.8513 1.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0423 3.5809 -0.3825 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4033 3.2325 -2.7997 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6306 1.0605 -3.8137 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5476 -0.6639 -2.4502 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7063 0.7696 1.3197 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4211 1.1546 -2.3851 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1597 -1.2031 -1.6759 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8018 -0.6678 -3.2795 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3561 -1.4721 -1.4512 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1938 0.3106 -2.2301 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7006 1.0604 1.4372 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7848 -1.0488 2.0773 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0498 -1.4361 1.6836 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4367 -2.7341 0.3397 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3871 -2.0335 -2.3655 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3378 -0.2651 -2.1700 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9028 -5.0459 -3.4323 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1703 -5.4313 -1.8081 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3996 -4.1526 -2.8605 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1428 0.5439 2.9623 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 2.8408 0.6022 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5045 2.5983 0.9428 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6702 2.7734 -0.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6424 3.9137 -0.3461 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5553 1.7720 -3.9522 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4286 2.8711 -2.4432 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5630 3.1884 -3.8902 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0605 1.0815 -4.2138 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0438 2.4147 -4.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9482 2.7688 -3.4219 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6192 6.3108 -1.1604 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7904 7.2679 0.1824 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9192 6.8000 -1.3818 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4652 1.8732 -1.9066 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5014 2.8375 -0.4387 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4620 1.3720 -0.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4599 -3.1419 2.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3783 -2.9540 4.4867 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0219 -0.7726 5.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7029 1.2525 4.3355 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8140 1.0729 2.1264 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4902 0.0679 -4.3364 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1714 -1.9450 0.9193 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 3 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 10 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 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 30 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 27 37 1 0 26 38 1 0 38 39 2 0 38 40 1 0 40 41 1 0 41 42 2 0 42 43 1 0 41 44 1 0 44 45 1 0 44 46 1 0 40 47 1 0 47 48 1 0 48 49 2 0 48 50 1 0 26 51 1 0 24 52 1 0 52 53 1 0 53 54 2 0 53 55 1 0 55 56 2 0 56 57 1 0 57 58 2 0 58 59 1 0 59 60 2 0 23 61 1 0 17 62 1 0 16 11 1 0 42 21 1 0 44 23 1 0 30 25 1 0 32 29 1 0 60 55 1 0 1 63 1 0 1 64 1 0 1 65 1 0 2 66 1 0 2 67 1 0 3 68 1 0 4 69 1 0 4 70 1 0 4 71 1 0 5 72 1 0 5 73 1 0 6 74 1 0 6 75 1 0 9 76 1 0 10 77 1 0 12 78 1 0 13 79 1 0 14 80 1 0 15 81 1 0 16 82 1 0 17 83 1 0 21 84 1 0 22 85 1 0 22 86 1 0 24 87 1 0 25 88 1 0 27 89 1 0 28 90 1 0 28 91 1 0 29 92 1 0 31 93 1 0 31 94 1 0 36 95 1 0 36 96 1 0 36 97 1 0 37 98 1 0 40 99 1 0 43100 1 0 43101 1 0 43102 1 0 45103 1 0 45104 1 0 45105 1 0 46106 1 0 46107 1 0 46108 1 0 50109 1 0 50110 1 0 50111 1 0 51112 1 0 51113 1 0 51114 1 0 56115 1 0 57116 1 0 58117 1 0 59118 1 0 60119 1 0 61120 1 0 62121 1 0 M END

Standard InCHIKey	LNTOLDCVMUNKRU-XCBLAXHTSA-N
Standard InCHI	InChI=1S/C47H59NO14/c1-9-25(2)20-21-34(52)48-36(29-16-12-10-13-17-29)37(53)43(56)60-31-23-47(57)41(61-42(55)30-18-14-11-15-19-30)39-45(8,32(51)22-33-46(39,24-58-33)62-28(5)50)40(54)38(59-27(4)49)35(26(31)3)44(47,6)7/h10-19,25,31-33,36-39,41,51,53,57H,9,20-24H2,1-8H3,(H,48,52)/t25?,31-,32-,33+,36?,37+,38+,39-,41-,45+,46-,47+/m0/s1
SMILES	CCC(C)CCC(=O)NC(C1=CC=CC=C1)C(C(=O)OC2CC3(C(C4C(C(CC5C4(CO5)OC(=O)C)O)(C(=O)C(C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	861.39	Volume:	869.915 ? Van der Waals volume.
Dense:	0.99	LogP:	4.063 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.722 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.277 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	18.0	Rigid Bonds:	38.0
TPSA:	221.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.126	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.109	Fsp³:	0.574
MCE-18:	164.216 ? 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:	0.627	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.043 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.385 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.0

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.049	MDCK Permeability:	-4.586
Pgp-inhibitor:	0.044	Pgp-substrate:	0.721
PAMPA:	1.0 ? 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):	0.561
20% Bioavailability (F20%):	0.968	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	91.599%	Volume Distribution (VD):	-0.063
Fu:	8.214% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.067
OATP1B3 inhibitor:	0.894	BCRP inhibitor:	0.0
BSEP inhibitor:	0.964

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.831	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.01	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.789
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.992 ? 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):

2.851

Half-life (T1/2):

2.326

ADMET: Toxicity

hERG Blockers:	0.032	hERG Blockers (10um):	0.318
Human Hepatotoxicity (H-HT):	0.858	Drug-induced Liver Injury (DILI):	0.972
AMES Toxicity:	0.754	Rat Oral Acute Toxicity:	0.563
Maximum Recommended Daily Dose:	0.919	Skin Sensitization:	0.802
Carcinogencity:	0.123	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.995	Ototoxicity:	0.99
Hematotoxicity:	0.034	Drug-induced Nephrotoxicity:	0.993
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.472
A549 Cytotoxicity:	0.108	Hek293 Cytotoxicity:	0.953
BCF:	0.542 ? 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:	3.674 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.637 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.618 ? 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
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[14987066]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844936]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24820	Taxus cuspidata	Species	Taxaceae	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 NPC328571 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	11866
0.1-0.2	35883
0.2-0.3	1979
0.3-0.4	63
0.4-0.5	12
0.5-0.6	26
0.6-0.7	7
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8842	High Similarity	NPC473400
0.8265	Intermediate Similarity	NPC603171
0.7767	Intermediate Similarity	NPC471606
0.7767	Intermediate Similarity	NPC275170
0.7723	Intermediate Similarity	NPC317882
0.7476	Intermediate Similarity	NPC324251
0.7476	Intermediate Similarity	NPC206211
0.7404	Intermediate Similarity	NPC487360
0.7404	Intermediate Similarity	NPC471629
0.7404	Intermediate Similarity	NPC306001
0.7353	Intermediate Similarity	NPC473300
0.7308	Intermediate Similarity	NPC33372
0.7308	Intermediate Similarity	NPC67246
0.7245	Intermediate Similarity	NPC603140
0.7238	Intermediate Similarity	NPC479182
0.7238	Intermediate Similarity	NPC479180
0.7212	Intermediate Similarity	NPC471623
0.7212	Intermediate Similarity	NPC208553
0.7212	Intermediate Similarity	NPC181964
0.7212	Intermediate Similarity	NPC307628
0.7037	Intermediate Similarity	NPC486061
0.7037	Intermediate Similarity	NPC486060
0.6972	Remote Similarity	NPC487361
0.6857	Remote Similarity	NPC36607
0.6327	Remote Similarity	NPC155329
0.6327	Remote Similarity	NPC114357
0.6126	Remote Similarity	NPC453583
0.6071	Remote Similarity	NPC471754
0.6018	Remote Similarity	NPC478329
0.5982	Remote Similarity	NPC453588
0.5929	Remote Similarity	NPC479183
0.5929	Remote Similarity	NPC479181
0.59	Remote Similarity	NPC605573
0.5893	Remote Similarity	NPC321072
0.5893	Remote Similarity	NPC215892
0.5893	Remote Similarity	NPC242662
0.5893	Remote Similarity	NPC102167
0.5893	Remote Similarity	NPC488127
0.5841	Remote Similarity	NPC191193
0.5752	Remote Similarity	NPC327699
0.5752	Remote Similarity	NPC473490
0.575	Remote Similarity	NPC472392
0.5645	Remote Similarity	NPC479184
0.5429	Remote Similarity	NPC259144
0.5429	Remote Similarity	NPC219419
0.5403	Remote Similarity	NPC472391
0.5366	Remote Similarity	NPC116862
0.536	Remote Similarity	NPC479185
0.5192	Remote Similarity	NPC197037
0.5192	Remote Similarity	NPC229545
0.5192	Remote Similarity	NPC248265
0.5192	Remote Similarity	NPC134685
0.5085	Remote Similarity	NPC478328
0.5048	Remote Similarity	NPC91730
0.5042	Remote Similarity	NPC473558

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC328571 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3462
0.1-0.2	5560
0.2-0.3	115
0.3-0.4	0
0.4-0.5	4
0.5-0.6	4
0.6-0.7	3
0.7-0.8	1
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
0.7212	Intermediate Similarity	NPD8485	Phase 4
0.6486	Remote Similarity	NPD8486	Phase 1
0.6364	Remote Similarity	NPD8368	Phase 2
0.6036	Remote Similarity	NPD8424	Phase 3
0.5984	Remote Similarity	NPD8462	Phase 2
0.5893	Remote Similarity	NPD8360	Approved
0.5893	Remote Similarity	NPD8361	Phase 4
0.5702	Remote Similarity	NPD8435	Phase 4

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