NPASS Compound

Natural Product: NPC67926

Natural Product ID	NPC67926
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MIJTXBNFQDJTPL-LDLQPGKCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11944608
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 93 96 0 0 0 0 0 0 0 0999 V2000 2.2436 0.6114 1.5047 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4875 0.2522 0.4852 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0157 0.1293 0.5896 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6069 1.4403 0.4452 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4258 2.0943 1.4929 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1464 3.2183 0.7049 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1080 2.6671 -0.2843 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5582 1.2380 0.0014 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9724 0.4652 0.9155 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9995 -0.8468 0.3461 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6611 -1.6212 0.4344 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5365 -0.9821 -0.2997 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9538 -0.6075 -1.6785 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5444 -2.0269 -0.5258 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8004 -1.4632 -1.1361 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1184 -0.0415 -0.8056 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5335 0.1024 -0.7082 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2095 0.9939 -1.5193 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5787 1.6863 -2.3521 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6582 1.1622 -1.4406 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4034 0.4807 -0.5988 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8393 0.5971 -0.4676 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4792 -0.2098 0.4874 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8380 -0.1451 0.6585 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5730 0.7346 -0.1312 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9482 1.5259 -1.0676 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5710 1.4536 -1.2337 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0657 -3.1534 -1.1717 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0885 -4.4566 -0.8019 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6394 -4.6991 0.2972 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4653 -5.6071 -1.5572 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2929 -1.8058 1.7558 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3208 -2.9408 2.5085 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7427 -3.9827 1.9708 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8509 -2.8744 3.9157 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3619 -1.1143 -0.9368 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2346 -2.1403 -1.2572 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7040 -2.8424 -0.3426 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5906 -2.3827 -2.6650 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5309 1.2723 2.1137 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1599 0.5170 3.3391 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6615 2.1910 2.6210 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7227 0.7596 -0.8307 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2312 3.5094 -0.4547 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5132 4.0268 -1.6923 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7858 3.7685 -2.7032 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6791 4.9282 -1.9766 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3135 0.6959 1.4208 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7824 0.8279 2.4508 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0889 -0.3341 1.6182 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2090 2.2178 0.2327 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1680 1.4731 -0.5189 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7867 2.5881 2.2530 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3134 3.7210 0.1172 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4962 4.0316 1.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6441 2.5950 -1.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6136 -1.5137 1.0305 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8984 -2.6061 0.0152 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1177 -0.4272 -2.3885 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6868 0.1454 -1.8572 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4032 -1.5697 -2.0898 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8789 -2.3688 0.4672 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8176 -1.5465 -2.2500 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6867 -2.0590 -0.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8272 0.6757 -1.6042 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1222 1.8654 -2.0929 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8448 -0.2259 0.0393 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8975 -0.8931 1.0987 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3446 -0.7688 1.3981 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6475 0.7685 0.0225 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5297 2.2074 -1.6783 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0927 2.0737 -1.9648 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6669 -5.2979 -2.6248 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2653 -6.4414 -1.5517 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4315 -5.9295 -1.1117 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2765 -2.8375 3.9674 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2386 -3.7607 4.4536 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2051 -1.9742 4.4545 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1277 -3.3492 -2.7426 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6613 -2.4469 -3.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2685 -1.5623 -2.9811 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7489 -0.3980 3.5134 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4624 1.0876 4.2914 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0762 0.4348 3.5516 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4682 2.1273 1.8623 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3458 3.1619 2.9370 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1703 1.7497 3.5350 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4257 0.1351 -0.2869 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3583 1.7274 -0.8746 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5296 0.6154 -1.8754 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4061 4.8820 -1.1654 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1712 4.6371 -2.9297 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3438 5.9843 -2.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 6 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 14 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 11 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 10 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 9 40 1 0 40 41 1 0 40 42 1 0 8 43 1 0 7 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 16 2 1 0 27 22 1 0 12 3 1 0 40 5 1 0 1 48 1 0 1 49 1 0 3 50 1 1 4 51 1 0 4 52 1 0 5 53 1 1 6 54 1 0 6 55 1 0 7 56 1 6 10 57 1 1 11 58 1 6 13 59 1 0 13 60 1 0 13 61 1 0 14 62 1 1 15 63 1 0 15 64 1 0 16 65 1 6 20 66 1 0 21 67 1 0 23 68 1 0 24 69 1 0 25 70 1 0 26 71 1 0 27 72 1 0 31 73 1 0 31 74 1 0 31 75 1 0 35 76 1 0 35 77 1 0 35 78 1 0 39 79 1 0 39 80 1 0 39 81 1 0 41 82 1 0 41 83 1 0 41 84 1 0 42 85 1 0 42 86 1 0 42 87 1 0 43 88 1 0 43 89 1 0 43 90 1 0 47 91 1 0 47 92 1 0 47 93 1 0 M END

Standard InCHIKey	MIJTXBNFQDJTPL-LDLQPGKCSA-N
Standard InCHI	InChI=1S/C37H46O10/c1-20-28-17-27-18-29(43-22(3)38)21(2)33(36(27,7)8)34(45-24(5)40)35(46-25(6)41)37(28,9)31(44-23(4)39)19-30(20)47-32(42)16-15-26-13-11-10-12-14-26/h10-16,27-31,34-35H,1,17-19H2,2-9H3/b16-15+/t27-,28+,29-,30-,31-,34+,35-,37-/m0/s1
SMILES	C=C1[C@H]2C[C@H]3C[C@@H](C(=C([C@H]([C@@H]([C@]2(C)[C@H](C[C@@H]1OC(=O)/C=C/c1ccccc1)OC(=O)C)OC(=O)C)OC(=O)C)C3(C)C)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	650.31	Volume:	673.183 ? Van der Waals volume.
Dense:	0.966	LogP:	3.684 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.355 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.03 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	30.0
TPSA:	131.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.157	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.663	Fsp³:	0.541
MCE-18:	116.316 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.935	Fluc inhibitor:	0.408 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.084 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.04 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.325	Promiscuous compounds:	0.161

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.981	MDCK Permeability:	-4.588
Pgp-inhibitor:	1.0	Pgp-substrate:	0.491
PAMPA:	0.092 ? 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%):	0.975	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.969
Plasma Protein Binding (PPB):	90.556%	Volume Distribution (VD):	-0.476
Fu:	8.038% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.924	BCRP inhibitor:	0.007
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.801
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.23
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.952
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.274 ? 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):

7.29

Half-life (T1/2):

0.578

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.13
Human Hepatotoxicity (H-HT):	0.818	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.956	Rat Oral Acute Toxicity:	0.526
Maximum Recommended Daily Dose:	0.982	Skin Sensitization:	1.0
Carcinogencity:	0.767	Eye Corrosion:	0.0
Eye Irritation:	0.061	Respiratory Toxicity:	0.11
Drug-induced Neurotoxicity:	0.958	Ototoxicity:	0.337
Hematotoxicity:	0.721	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.203
A549 Cytotoxicity:	0.904	Hek293 Cytotoxicity:	0.661
BCF:	0.774 ? 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:	3.969 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.928 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.426 ? 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
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[11473432]
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.	Japan	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[8991951]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644081]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	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[TCM_Taiwan]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23720	Taxus wallichiana	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 NPC67926 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	13185
0.1-0.2	33592
0.2-0.3	2852
0.3-0.4	181
0.4-0.5	30
0.5-0.6	11
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC300827
0.7671	Intermediate Similarity	NPC45821
0.7639	Intermediate Similarity	NPC89324
0.7297	Intermediate Similarity	NPC473439
0.7105	Intermediate Similarity	NPC471758
0.7013	Intermediate Similarity	NPC260194
0.6883	Remote Similarity	NPC284022
0.6203	Remote Similarity	NPC195224
0.593	Remote Similarity	NPC266374
0.5875	Remote Similarity	NPC473749
0.5663	Remote Similarity	NPC12016
0.5542	Remote Similarity	NPC604529
0.5405	Remote Similarity	NPC284194
0.5349	Remote Similarity	NPC472373
0.5294	Remote Similarity	NPC475128
0.5278	Remote Similarity	NPC486046
0.5176	Remote Similarity	NPC607515
0.5116	Remote Similarity	NPC58061
0.5057	Remote Similarity	NPC209851

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC67926 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3812
0.1-0.2	5199
0.2-0.3	139
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