NPASS Compound

Natural Product: NPC221289

Natural Product ID	NPC221289
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RJFFPCHJOFXZQD-YTSXHMEESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	71623698
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 103111 0 0 0 0 0 0 0 0999 V2000 3.3253 3.3702 -0.7105 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6121 4.4343 -0.1563 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5450 4.6273 1.2018 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2138 3.7248 2.0104 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9099 2.6849 1.4402 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9941 2.4652 0.0851 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7070 1.3250 -0.4820 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9011 1.6734 -1.3527 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6188 0.3842 -1.6963 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7192 -0.7989 -1.7405 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2616 -2.0370 -1.9593 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4765 -3.1711 -2.0184 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0842 -3.0798 -1.8539 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -1.8607 -1.6362 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1179 -1.7048 -1.4710 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5915 -1.3505 -0.1510 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3133 -1.3681 1.0017 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6795 -0.9457 2.1525 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3597 -0.5196 2.1484 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3756 -0.5018 0.9855 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7298 -0.0984 0.9090 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8854 1.1270 0.0780 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8869 1.9659 -0.3093 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2119 3.0439 -1.1241 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5094 3.2790 -1.5439 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4927 2.4100 -1.1305 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2077 1.3454 -0.3310 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1247 0.4182 0.1422 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0743 -0.0005 1.4952 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0267 0.7553 2.3205 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8725 0.1544 3.2435 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7672 0.8842 3.9932 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8349 2.2647 3.8299 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0070 2.8842 2.9210 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1334 2.1184 2.1987 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0827 4.2573 2.7664 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7582 2.9393 4.6179 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5756 0.2196 4.8913 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6490 -0.0146 2.0388 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5695 -1.1785 2.8074 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8461 4.3696 -2.3729 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4118 1.7326 0.1123 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2830 -0.9298 -0.1533 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3895 -0.9553 -1.4226 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1888 -2.1255 -2.2415 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3312 -3.0253 -2.1589 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6117 -2.5093 -2.3866 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7284 -3.3129 -2.3065 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6322 -4.6660 -1.9971 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3750 -5.1717 -1.7738 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2350 -4.3473 -1.8570 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2595 -6.5262 -1.4623 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7698 -5.4754 -1.9185 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0251 -2.8155 -2.5321 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1661 -2.7066 -2.0584 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6453 -3.1788 -3.3077 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2702 -0.0954 3.2960 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6555 -1.7978 1.0307 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3566 -0.7392 -1.5833 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8566 0.5500 -1.3586 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3894 -4.2988 -1.9300 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6488 -2.1612 -2.1277 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7645 2.4225 -0.5558 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1431 3.9224 3.3794 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8291 5.6917 1.7641 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3439 3.2694 -1.7918 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0777 5.1582 -0.7665 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4473 1.9578 2.0718 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1323 0.7335 0.3474 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5822 2.2387 -2.2457 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1402 0.5689 -2.6495 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3984 0.1419 -0.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9343 -4.1501 -2.1973 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8906 -0.7415 -2.0873 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2281 -0.9538 3.0656 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2260 -0.9041 0.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4013 3.7247 -1.4356 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5416 2.5462 -1.4353 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4780 -1.0593 1.4479 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8127 -0.9267 3.3709 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4896 2.6208 1.5023 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1997 4.7607 1.9172 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7594 3.9565 4.6768 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4395 0.5593 5.2462 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5633 0.8538 2.7019 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9559 -1.9717 2.3960 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3710 4.1280 -3.2218 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7793 2.2824 0.8578 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1539 -1.6469 -3.2895 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6881 -1.4604 -2.6265 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3133 -4.8490 -1.6686 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3211 -6.9019 -1.3784 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7479 -6.4800 -2.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3718 -2.8842 -3.4818 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1065 -3.6095 -1.4278 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9286 -3.7786 -3.6438 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0063 0.8284 3.6728 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7541 -2.8051 1.0814 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7599 -5.0745 -2.4504 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2285 -1.6223 -1.5183 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5669 3.3912 -0.5764 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9531 4.1933 3.9167 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9338 5.9293 2.7499 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 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 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 33 37 1 0 32 38 1 0 29 39 1 0 39 40 1 0 25 41 1 0 23 42 1 0 20 43 2 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 50 52 1 0 49 53 1 0 48 54 1 0 45 55 1 0 55 56 1 0 19 57 1 0 17 58 1 0 14 59 2 0 59 60 1 0 13 61 1 0 11 62 1 0 8 63 1 0 4 64 1 0 3 65 1 0 6 1 1 0 60 7 1 0 59 10 1 0 55 15 1 0 43 16 1 0 51 46 1 0 39 21 1 0 27 22 1 0 35 30 1 0 1 66 1 0 2 67 1 0 5 68 1 0 7 69 1 1 8 70 1 6 9 71 1 0 9 72 1 0 12 73 1 0 15 74 1 6 18 75 1 0 21 76 1 6 24 77 1 0 26 78 1 0 29 79 1 6 31 80 1 0 35 81 1 0 36 82 1 0 37 83 1 0 38 84 1 0 39 85 1 1 40 86 1 0 41 87 1 0 42 88 1 0 45 89 1 6 47 90 1 0 51 91 1 0 52 92 1 0 53 93 1 0 54 94 1 0 55 95 1 1 56 96 1 0 57 97 1 0 58 98 1 0 61 99 1 0 62100 1 0 63101 1 0 64102 1 0 65103 1 0 M END

Standard InCHIKey	RJFFPCHJOFXZQD-YTSXHMEESA-N
Standard InCHI	InChI=1S/C45H38O20/c46-16-8-21(50)31-30(9-16)63-42(14-4-25(54)37(59)26(55)5-14)39(61)35(31)33-23(52)12-24(53)34-36(40(62)43(65-45(33)34)15-6-27(56)38(60)28(57)7-15)32-22(51)11-19(48)17-10-29(58)41(64-44(17)32)13-1-2-18(47)20(49)3-13/h1-9,11-12,29,35-36,39-43,46-62H,10H2/t29-,35-,36+,39-,40-,41+,42+,43+/m0/s1
SMILES	c1cc(c(cc1[C@@H]1[C@H](Cc2c(cc(c([C@@H]3c4c(cc(c([C@@H]5c6c(cc(cc6O[C@H](c6cc(c(c(c6)O)O)O)[C@H]5O)O)O)c4O[C@H](c4cc(c(c(c4)O)O)O)[C@H]3O)O)O)c2O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	898.2	Volume:	838.216 ? Van der Waals volume.
Dense:	1.072	LogP:	0.812 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.277 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.056 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	51.0
TPSA:	371.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	17.0	Rings:	9.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.109	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.557	Fsp³:	0.2
MCE-18:	200.0 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.842	Fluc inhibitor:	0.178 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.163 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.513 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.638	Promiscuous compounds:	0.284

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.929	MDCK Permeability:	-4.754
Pgp-inhibitor:	0.0	Pgp-substrate:	0.011
PAMPA:	0.869 ? 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):	0.004
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.998
Plasma Protein Binding (PPB):	86.988%	Volume Distribution (VD):	0.262
Fu:	16.181% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.029
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.743	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

3.221

Half-life (T1/2):

7.771

ADMET: Toxicity

hERG Blockers:	0.159	hERG Blockers (10um):	0.975
Human Hepatotoxicity (H-HT):	0.948	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.146	Rat Oral Acute Toxicity:	0.235
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.214	Respiratory Toxicity:	0.93
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.004
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.002
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.992
BCF:	0.983 ? 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:	3.576 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.761 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.058 ? 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
NPO16913	Helianthus maximiliani	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18664	Ageratina dendroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24263	Cornus kousa	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14990	Ectyoplasia ferox	Species	Raspailiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16913	Helianthus maximiliani	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28816	Capnoides sempervirens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17446	Cassia kleinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16913	Helianthus maximiliani	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17446	Cassia kleinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11782	Vateria indica	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19295	Bromelia plumieri	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18664	Ageratina dendroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24263	Cornus kousa	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28816	Capnoides sempervirens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16913	Helianthus maximiliani	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14990	Ectyoplasia ferox	Species	Raspailiidae	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 NPC221289 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	22062
0.1-0.2	24755
0.2-0.3	2700
0.3-0.4	178
0.4-0.5	71
0.5-0.6	24
0.6-0.7	28
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	11
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC246202
0.9333	High Similarity	NPC224161
0.9333	High Similarity	NPC46335
0.9333	High Similarity	NPC279406
0.9333	High Similarity	NPC486519
0.9167	High Similarity	NPC58190
0.9167	High Similarity	NPC108811
0.9167	High Similarity	NPC170103
0.9167	High Similarity	NPC236202
0.9167	High Similarity	NPC262911
0.9167	High Similarity	NPC202742
0.8833	High Similarity	NPC96576
0.8358	Intermediate Similarity	NPC278548
0.8209	Intermediate Similarity	NPC600630
0.8209	Intermediate Similarity	NPC607896
0.8209	Intermediate Similarity	NPC611369
0.7794	Intermediate Similarity	NPC226809
0.7612	Intermediate Similarity	NPC313116
0.7612	Intermediate Similarity	NPC603340
0.7536	Intermediate Similarity	NPC601997
0.7536	Intermediate Similarity	NPC609211
0.7536	Intermediate Similarity	NPC610665
0.7391	Intermediate Similarity	NPC70409
0.7391	Intermediate Similarity	NPC204770
0.7391	Intermediate Similarity	NPC600551
0.7391	Intermediate Similarity	NPC601980
0.7391	Intermediate Similarity	NPC602065
0.7391	Intermediate Similarity	NPC611024
0.7286	Intermediate Similarity	NPC211561
0.7179	Intermediate Similarity	NPC212614
0.7179	Intermediate Similarity	NPC205613
0.7143	Intermediate Similarity	NPC86630
0.7105	Intermediate Similarity	NPC147743
0.7105	Intermediate Similarity	NPC4809
0.7105	Intermediate Similarity	NPC73517
0.7059	Intermediate Similarity	NPC294558
0.7059	Intermediate Similarity	NPC18185
0.7059	Intermediate Similarity	NPC263940
0.7051	Intermediate Similarity	NPC106601
0.7051	Intermediate Similarity	NPC151474
0.6719	Remote Similarity	NPC178054
0.6711	Remote Similarity	NPC135021
0.6707	Remote Similarity	NPC159526
0.6667	Remote Similarity	NPC601999
0.6533	Remote Similarity	NPC44192
0.6452	Remote Similarity	NPC261619
0.6452	Remote Similarity	NPC61477
0.6452	Remote Similarity	NPC78770
0.6452	Remote Similarity	NPC219876
0.6452	Remote Similarity	NPC126029
0.6452	Remote Similarity	NPC15658
0.64	Remote Similarity	NPC65333
0.64	Remote Similarity	NPC302549
0.625	Remote Similarity	NPC9309
0.625	Remote Similarity	NPC184245
0.625	Remote Similarity	NPC187801
0.625	Remote Similarity	NPC610920
0.6234	Remote Similarity	NPC20050
0.622	Remote Similarity	NPC78074
0.6154	Remote Similarity	NPC306267
0.6129	Remote Similarity	NPC268266
0.6129	Remote Similarity	NPC42760
0.6129	Remote Similarity	NPC220825
0.6129	Remote Similarity	NPC268342
0.6053	Remote Similarity	NPC272552
0.6053	Remote Similarity	NPC226108
0.6053	Remote Similarity	NPC322899
0.6024	Remote Similarity	NPC478340
0.5974	Remote Similarity	NPC46283
0.5974	Remote Similarity	NPC469944
0.5972	Remote Similarity	NPC277331
0.5972	Remote Similarity	NPC100482
0.5952	Remote Similarity	NPC478337
0.5952	Remote Similarity	NPC478338
0.5949	Remote Similarity	NPC478616
0.5949	Remote Similarity	NPC478339
0.5795	Remote Similarity	NPC478617
0.557	Remote Similarity	NPC134911
0.5541	Remote Similarity	NPC82917
0.5422	Remote Similarity	NPC471404
0.5402	Remote Similarity	NPC479793
0.5395	Remote Similarity	NPC165483
0.5385	Remote Similarity	NPC207179
0.5385	Remote Similarity	NPC167571
0.5385	Remote Similarity	NPC278552
0.5325	Remote Similarity	NPC28440
0.5281	Remote Similarity	NPC479794
0.5256	Remote Similarity	NPC155564
0.5244	Remote Similarity	NPC98583
0.507	Remote Similarity	NPC171932
0.5065	Remote Similarity	NPC20757
0.5065	Remote Similarity	NPC227516

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC221289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4601
0.1-0.2	4507
0.2-0.3	33
0.3-0.4	6
0.4-0.5	1
0.5-0.6	0
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	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6452	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1613	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