NPASS Compound

Natural Product: NPC479000

Natural Product ID	NPC479000
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AKGSKBKBENKBOP-LWDNIVNZSA-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:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

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 109112 0 0 0 0 0 0 0 0999 V2000 10.3146 0.1457 -3.8627 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4564 -0.9733 -4.4243 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0245 -0.6796 -4.0652 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8868 -0.6030 -2.5725 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2553 -1.8390 -1.8359 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0842 -1.7273 -0.3311 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6482 -1.4351 -0.0417 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3660 -1.3254 1.4702 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1724 -0.2440 2.0286 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6919 0.8008 2.6253 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2572 1.0765 2.8419 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0230 1.1735 4.3101 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6715 1.4761 4.7999 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5325 0.6110 4.5561 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0414 0.2873 3.2111 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6436 1.4392 2.3639 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1545 1.1110 0.9894 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0500 0.2812 0.9160 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4883 -0.1560 -0.1915 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7471 -0.0509 2.0352 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9189 -0.8356 2.0979 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9531 -0.1421 1.2960 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4711 -0.7723 0.2717 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5254 -0.3804 -0.7459 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0204 -1.6137 -1.3927 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3424 -1.6718 -2.8535 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3546 -0.4675 -3.7248 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0115 -2.9608 -3.6247 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4075 -1.7248 -1.7968 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3184 -0.5959 -1.5453 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7087 0.6756 -1.0859 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8212 1.4323 -0.3370 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5438 0.5214 -0.1450 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0954 1.8420 0.2947 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4235 3.0088 -0.5158 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6053 3.9921 -0.1751 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5540 5.3934 -0.7285 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6777 3.5252 0.8578 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0577 4.1117 1.7323 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6424 2.0479 0.5980 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2706 1.2294 1.7804 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7919 1.8906 -0.4831 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0730 -0.2013 0.9585 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0619 -3.0075 -1.7340 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1997 -3.7132 -0.5728 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7489 -3.2537 0.4976 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8854 -5.0253 -0.5849 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3590 -0.0152 -4.2539 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9396 1.1322 -4.1623 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3589 0.0749 -2.7731 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5798 -1.0418 -5.5339 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7272 -1.9593 -4.0121 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3374 -1.4930 -4.4333 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6838 0.2639 -4.5629 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7902 -0.4072 -2.3840 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3929 0.2897 -2.1457 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6552 -2.6886 -2.2304 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3179 -2.1027 -2.0794 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7893 -1.0380 0.1237 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2969 -2.7478 0.0829 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3433 -0.4166 -0.4249 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9531 -2.1751 -0.4524 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2785 -1.2375 1.5322 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6953 -2.3030 1.9568 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2953 -0.3023 1.9469 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3917 1.5654 3.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6623 0.2808 2.4363 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0692 2.0679 2.3468 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6906 2.0241 4.6652 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4692 0.2877 4.8300 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4846 2.5675 4.5669 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7806 1.5331 5.9431 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7521 -0.3903 5.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6638 0.9809 5.1988 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5810 -0.5025 2.6658 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0349 -0.2574 3.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8932 2.1069 2.8244 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5557 2.0893 2.2169 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9352 0.6222 0.3609 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9100 2.0519 0.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1919 -0.8804 3.1888 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6776 -1.8367 1.6817 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0503 -1.7825 0.1331 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9599 0.1928 -1.5229 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5691 -2.5886 -1.0239 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7578 0.3850 -3.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4378 -0.1922 -3.8918 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9849 -0.6764 -4.7742 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6477 -3.7281 -2.9283 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1693 -2.6992 -4.2988 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9075 -3.2902 -4.1848 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9356 -0.3586 -2.4583 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0713 -0.9199 -0.7796 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4747 1.2893 -1.9784 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4983 0.6808 0.1722 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4880 1.9731 -1.0402 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4435 2.0594 0.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5979 2.0478 1.2996 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1745 3.1748 -1.2897 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5888 5.7702 -0.7956 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9747 6.0487 -0.0692 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1596 5.3798 -1.7847 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1725 1.1738 2.4578 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4763 1.6972 2.3624 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1094 2.4326 -1.2369 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3883 -0.7857 1.3560 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1851 -5.7776 -0.9980 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2287 -5.2989 0.4414 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8011 -5.0236 -1.2251 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 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 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 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 26 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 36 37 1 0 36 38 1 0 38 39 2 0 38 40 1 0 40 41 1 0 40 42 1 6 33 43 1 1 29 44 1 1 44 45 1 0 45 46 2 0 45 47 1 0 41 22 1 0 33 24 1 0 40 34 1 0 29 25 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 0 2 52 1 0 3 53 1 0 3 54 1 0 4 55 1 0 4 56 1 0 5 57 1 0 5 58 1 0 6 59 1 0 6 60 1 0 7 61 1 0 7 62 1 0 8 63 1 0 8 64 1 0 9 65 1 0 10 66 1 0 11 67 1 0 11 68 1 0 12 69 1 0 12 70 1 0 13 71 1 0 13 72 1 0 14 73 1 0 14 74 1 0 15 75 1 0 15 76 1 0 16 77 1 0 16 78 1 0 17 79 1 0 17 80 1 0 21 81 1 0 21 82 1 0 23 83 1 0 24 84 1 6 25 85 1 1 27 86 1 0 27 87 1 0 27 88 1 0 28 89 1 0 28 90 1 0 28 91 1 0 30 92 1 0 30 93 1 0 31 94 1 6 32 95 1 0 32 96 1 0 32 97 1 0 34 98 1 1 35 99 1 0 37100 1 0 37101 1 0 37102 1 0 41103 1 0 41104 1 0 42105 1 0 43106 1 0 47107 1 0 47108 1 0 47109 1 0 M END

Standard InCHIKey	AKGSKBKBENKBOP-LWDNIVNZSA-N
Standard InCHI	InChI=1S/C40H62O7/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-34(42)46-27-31-24-32-35-37(5,6)39(35,47-30(4)41)25-29(3)40(32,45)33-23-28(2)36(43)38(33,44)26-31/h14-15,23-24,29,32-33,35,44-45H,7-13,16-22,25-27H2,1-6H3/b15-14-/t29-,32+,33-,35-,38-,39+,40-/m1/s1
SMILES	CCCCCCCC/C=CCCCCCCCC(=O)OCC1=C[C@H]2[C@@H]3C(C)(C)[C@@]3(C[C@@H](C)[C@@]2([C@@H]2C=C(C)C(=O)[C@]2(C1)O)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.45	Volume:	711.883 ? Van der Waals volume.
Dense:	0.919	LogP:	7.436 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.751 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.216 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	20.0	Rigid Bonds:	22.0
TPSA:	110.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.087	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.987	Fsp³:	0.775
MCE-18:	75.296 ? 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:	0.583	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.266	Promiscuous compounds:	0.568

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.186	MDCK Permeability:	-4.793
Pgp-inhibitor:	0.655	Pgp-substrate:	0.003
PAMPA:	0.008 ? 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):	0.005
20% Bioavailability (F20%):	0.969	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.999
Plasma Protein Binding (PPB):	97.774%	Volume Distribution (VD):	-0.264
Fu:	1.602% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.983
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.082
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.991	CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.131	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.065 ? 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):

4.588

Half-life (T1/2):

0.912

ADMET: Toxicity

hERG Blockers:	0.219	hERG Blockers (10um):	0.612
Human Hepatotoxicity (H-HT):	0.371	Drug-induced Liver Injury (DILI):	0.052
AMES Toxicity:	0.461	Rat Oral Acute Toxicity:	0.292
Maximum Recommended Daily Dose:	0.677	Skin Sensitization:	1.0
Carcinogencity:	0.658	Eye Corrosion:	0.034
Eye Irritation:	0.437	Respiratory Toxicity:	0.618
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.246
Hematotoxicity:	0.079	Drug-induced Nephrotoxicity:	0.894
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.176
A549 Cytotoxicity:	0.858	Hek293 Cytotoxicity:	0.628
BCF:	1.421 ? 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:	5.501 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.885 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.949 ? 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
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28445049]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Agarwood	n.a.	n.a.	PMID[29083898]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30672698]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320738]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	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	4
Activity	1

Activity Type	# Activity
Cell line	5

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
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[28445049]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[28445049]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[28445049]
NPT2740	Cell line	Neutrophils	n.a.	Activity	=	18.1	%	PMID[28445049]
NPT2740	Cell line	Neutrophils	n.a.	IC50	>	10000.0	nM	PMID[28445049]

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 NPC479000 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	17387
0.1-0.2	30671
0.2-0.3	1616
0.3-0.4	105
0.4-0.5	27
0.5-0.6	17
0.6-0.7	15
0.7-0.8	0
0.8-0.85	0
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC170212
0.8657	High Similarity	NPC17138
0.8657	High Similarity	NPC101825
0.8657	High Similarity	NPC215643
0.8657	High Similarity	NPC265499
0.8529	High Similarity	NPC221511
0.7727	Intermediate Similarity	NPC96739
0.7671	Intermediate Similarity	NPC151216
0.7671	Intermediate Similarity	NPC89227
0.7237	Intermediate Similarity	NPC257017
0.7162	Intermediate Similarity	NPC485731
0.7162	Intermediate Similarity	NPC485732
0.7143	Intermediate Similarity	NPC174471
0.6962	Remote Similarity	NPC162009
0.6944	Remote Similarity	NPC474871
0.6944	Remote Similarity	NPC260786
0.6712	Remote Similarity	NPC485736
0.6712	Remote Similarity	NPC277477
0.6712	Remote Similarity	NPC479003
0.6712	Remote Similarity	NPC485735
0.6712	Remote Similarity	NPC485733
0.6329	Remote Similarity	NPC183540
0.6316	Remote Similarity	NPC482454
0.622	Remote Similarity	NPC153651
0.6197	Remote Similarity	NPC153036
0.6197	Remote Similarity	NPC91189
0.6098	Remote Similarity	NPC602538
0.6024	Remote Similarity	NPC159692
0.5904	Remote Similarity	NPC222307
0.5679	Remote Similarity	NPC475391
0.56	Remote Similarity	NPC158523
0.5542	Remote Similarity	NPC474937
0.5488	Remote Similarity	NPC482317
0.5455	Remote Similarity	NPC71889
0.5455	Remote Similarity	NPC475937
0.5301	Remote Similarity	NPC477091
0.5287	Remote Similarity	NPC472760
0.5233	Remote Similarity	NPC124676
0.5125	Remote Similarity	NPC478681
0.5116	Remote Similarity	NPC484333
0.506	Remote Similarity	NPC275696
0.506	Remote Similarity	NPC255081
0.5056	Remote Similarity	NPC146280
0.5051	Remote Similarity	NPC102367
0.5051	Remote Similarity	NPC478683

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479000 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6521
0.1-0.2	2548
0.2-0.3	81
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