NPASS Compound

Natural Product: NPC218161

Natural Product ID	NPC218161
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Kaempferol-3-O-(2'',6''-Di-E-P-Coumaroyl)-Beta-Glucopyranoside
IUPAC Name	[(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4-dihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3628129
PubChem CID	10439991
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl glycosides

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 86 91 0 0 0 0 0 0 0 0999 V2000 -2.4767 -0.8636 -2.0530 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4328 -0.1295 -1.7162 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2972 1.2072 -1.8517 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2077 1.9079 -2.3238 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9115 1.8206 -1.5981 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3608 0.5436 -1.6484 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9117 0.5676 -1.0621 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4759 -0.6955 -0.9714 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2740 -1.6647 -0.0202 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4966 -2.7582 -0.2775 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3431 -3.6281 0.7250 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8753 -3.5129 1.9062 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6695 -2.4391 2.2188 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8701 -1.5039 1.2419 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5866 -0.4918 1.4556 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2410 -2.3132 3.4868 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0297 -1.2037 3.7298 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9942 -3.2910 4.4276 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1992 -4.3885 4.1490 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6512 -4.4813 2.8880 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9403 -5.3815 5.0809 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1657 -3.0501 -1.5503 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0969 -2.4453 -2.7450 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6097 -2.7654 -3.9082 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6079 -3.7147 -3.8893 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8894 -4.3376 -2.6944 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1709 -3.9995 -1.5530 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3188 -4.0404 -5.0536 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8911 1.4151 -1.8695 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2068 2.3591 -2.7848 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0033 2.9134 -2.0787 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4481 3.7544 -1.0612 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9049 1.8377 -4.0370 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7182 2.1286 -0.9782 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0413 1.7740 -0.8187 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4434 0.7772 -1.5217 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0007 2.4243 0.0656 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7714 3.4455 0.8461 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7634 4.0650 1.7172 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0560 3.6003 1.8032 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9841 4.2155 2.6640 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6520 5.2869 3.4432 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3464 5.7612 3.3598 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4446 5.1522 2.5141 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5644 5.9042 4.3018 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6686 -0.7724 -1.1836 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7003 -0.0397 -0.8288 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8966 -0.6382 -0.3122 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9690 0.1874 0.0178 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1379 -0.3357 0.5272 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2770 -1.7098 0.7262 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1993 -2.4894 0.3897 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0096 -1.9871 -0.1260 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4541 -2.2328 1.2385 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0127 1.4918 -3.3743 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5015 2.9940 -2.4898 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0645 2.0600 -0.4843 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7707 0.9829 -0.0344 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0298 -1.2960 3.7355 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4254 -3.2097 5.4033 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0250 -5.3313 2.6423 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4481 -6.2585 5.0106 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8744 -1.7092 -2.8256 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4005 -2.2808 -4.8575 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6742 -5.0794 -2.6925 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4224 -4.5090 -0.6384 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9878 -4.7727 -5.6732 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5384 0.7148 -2.4524 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8563 3.2559 -2.9985 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5513 3.5712 -2.7911 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2543 3.9160 -0.3868 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4145 2.4791 -4.5902 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0392 2.0383 0.1023 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7663 3.8618 0.8423 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3957 2.7734 1.2333 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0080 3.8508 2.7390 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0830 6.6074 3.9743 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4173 5.5034 2.4246 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5443 5.9112 4.0412 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6413 -1.8452 -1.1187 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6176 1.0275 -0.9349 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9053 1.2573 -0.1158 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9595 0.3284 0.7760 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2553 -3.5620 0.5263 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2027 -2.6961 -0.3598 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3132 -1.8196 0.8815 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 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 13 16 1 0 16 17 1 0 16 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 10 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 25 28 1 0 7 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 30 33 1 0 29 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 42 45 1 0 2 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 51 54 1 0 31 5 1 0 44 39 1 0 53 48 1 0 14 9 1 0 27 22 1 0 20 12 1 0 4 55 1 0 4 56 1 0 5 57 1 1 7 58 1 1 17 59 1 0 18 60 1 0 20 61 1 0 21 62 1 0 23 63 1 0 24 64 1 0 26 65 1 0 27 66 1 0 28 67 1 0 29 68 1 6 30 69 1 6 31 70 1 6 32 71 1 0 33 72 1 0 37 73 1 0 38 74 1 0 40 75 1 0 41 76 1 0 43 77 1 0 44 78 1 0 45 79 1 0 46 80 1 0 47 81 1 0 49 82 1 0 50 83 1 0 52 84 1 0 53 85 1 0 54 86 1 0 M END

Standard InCHIKey	YXXQUJGFZPLXJV-AIBWQOBZSA-N
Standard InCHI	InChI=1S/C39H32O15/c40-23-9-1-20(2-10-23)5-15-30(45)50-19-29-33(47)35(49)38(53-31(46)16-6-21-3-11-24(41)12-4-21)39(52-29)54-37-34(48)32-27(44)17-26(43)18-28(32)51-36(37)22-7-13-25(42)14-8-22/h1-18,29,33,35,38-44,47,49H,19H2/b15-5+,16-6+/t29-,33-,35+,38-,39+/m1/s1
SMILES	O=C(OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C/c1ccc(cc1)O)/C=C/c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	740.17	Volume:	716.158 ? Van der Waals volume.
Dense:	1.034	LogP:	3.227 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.653 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.076 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	40.0
TPSA:	242.88 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.08	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.507	Fsp³:	0.154
MCE-18:	122.444 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.999	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.879 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.781 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.347	Promiscuous compounds:	0.771

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.379	MDCK Permeability:	-5.033
Pgp-inhibitor:	0.053	Pgp-substrate:	0.006
PAMPA:	0.952 ? 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):	0.0
20% Bioavailability (F20%):	0.899	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	94.22%	Volume Distribution (VD):	-0.155
Fu:	7.126% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.331
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.683
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.685
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.021	CYP2D6-substrate:	0.945
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.851 ? 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):

2.754

Half-life (T1/2):

2.951

ADMET: Toxicity

hERG Blockers:	0.147	hERG Blockers (10um):	0.608
Human Hepatotoxicity (H-HT):	0.565	Drug-induced Liver Injury (DILI):	0.936
AMES Toxicity:	0.659	Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.94	Skin Sensitization:	0.999
Carcinogencity:	0.172	Eye Corrosion:	0.0
Eye Irritation:	0.806	Respiratory Toxicity:	0.061
Drug-induced Neurotoxicity:	0.036	Ototoxicity:	0.287
Hematotoxicity:	0.005	Drug-induced Nephrotoxicity:	0.122
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.081
A549 Cytotoxicity:	0.613	Hek293 Cytotoxicity:	0.989
BCF:	0.845 ? 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:	4.225 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.903 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.783 ? 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
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075766]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11112781]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[153409]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568769]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[17190463]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17870137]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[18239317]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[18239317]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18462007]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21417376]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21673922]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21848268]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	Urup Island (4557,9 N; 15044,9 E; depth 66 m)	2008-AUG	PMID[21848268]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23265519]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23317005]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23488669]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27524650]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29115831]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31182315]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31287310]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4955234]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8808	Artemisia schimperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11558	Atylosia trinervia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27848	Conoideocrella luteorostrata	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9930	Dendrodoris tuberculosa	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12893	Dermolepida albohirtum	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8777	Euryops algoensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4544	Gomortega keule	Species	Gomortegaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11949	Iris ensata	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6259	Keiferia lycopersicella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12317	Naja kaouthia	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12677	Penicillium kapuscinskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13002	Petasites georgicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1038	Phoenix loureiroi	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7050	Picea mariana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11709	Salvia parryi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12081	Streptomyces xanthochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10613	Thalictrum longistylum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8492	Viburnum urceolatum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7347	Viguiera oblongifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4293	Allium neapolitanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2968	Anthopleura xanthogrammica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19333	Byssothecium obiones	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4816	Cycas armstrongii	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25775	Dasystenella acanthina	Species	Primnoidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1897	Ephedra aphylla	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO115	Eutreptia viridis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6302	Licaria armeniaca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6130	Mammillaria magnimamma	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3756	Munronia delavayi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2609	Neonectria candida	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18463	Plectocephalus chilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3419	Quercus suber	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO291	Suillus bovinus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10870	Trichilia hirta	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10613	Thalictrum longistylum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4293	Allium neapolitanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6302	Licaria armeniaca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8492	Viburnum urceolatum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1897	Ephedra aphylla	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27848	Conoideocrella luteorostrata	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1038	Phoenix loureiroi	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9930	Dendrodoris tuberculosa	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19333	Byssothecium obiones	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12677	Penicillium kapuscinskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3756	Munronia delavayi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2609	Neonectria candida	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6259	Keiferia lycopersicella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12081	Streptomyces xanthochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12893	Dermolepida albohirtum	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO115	Eutreptia viridis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4544	Gomortega keule	Species	Gomortegaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6130	Mammillaria magnimamma	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4816	Cycas armstrongii	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11709	Salvia parryi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18463	Plectocephalus chilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8777	Euryops algoensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11949	Iris ensata	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO291	Suillus bovinus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7050	Picea mariana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10870	Trichilia hirta	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13002	Petasites georgicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7347	Viguiera oblongifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25775	Dasystenella acanthina	Species	Primnoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11558	Atylosia trinervia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12317	Naja kaouthia	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10613	Thalictrum longistylum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8808	Artemisia schimperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3419	Quercus suber	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2968	Anthopleura xanthogrammica	Species	Actiniidae	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
Ki	5

Activity Type	# Activity
Individual protein	5

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT233	Individual protein	Carbonic anhydrase II	Homo sapiens	Ki	=	8790.2	nM	PMID[26498393]
NPT1062	Individual protein	Carbonic anhydrase IV	Homo sapiens	Ki	=	344.2	nM	PMID[26498393]
NPT955	Individual protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	4.7	nM	PMID[26498393]
NPT949	Individual protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	408.9	nM	PMID[26498393]
NPT947	Individual protein	Carbonic anhydrase I	Homo sapiens	Ki	>	10000.0	nM	PMID[26498393]

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 NPC218161 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	14569
0.1-0.2	30980
0.2-0.3	3395
0.3-0.4	565
0.4-0.5	180
0.5-0.6	92
0.6-0.7	47
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	Natural Product ID
0.7849	Intermediate Similarity	NPC85751
0.7849	Intermediate Similarity	NPC19240
0.7766	Intermediate Similarity	NPC260504
0.7766	Intermediate Similarity	NPC89809
0.7723	Intermediate Similarity	NPC162394
0.7604	Intermediate Similarity	NPC96605
0.7604	Intermediate Similarity	NPC280642
0.7553	Intermediate Similarity	NPC221288
0.7553	Intermediate Similarity	NPC194836
0.7553	Intermediate Similarity	NPC91493
0.7553	Intermediate Similarity	NPC605081
0.732	Intermediate Similarity	NPC223426
0.7245	Intermediate Similarity	NPC478277
0.7245	Intermediate Similarity	NPC214621
0.7245	Intermediate Similarity	NPC34267
0.7245	Intermediate Similarity	NPC478276
0.7245	Intermediate Similarity	NPC478275
0.7245	Intermediate Similarity	NPC92815
0.7129	Intermediate Similarity	NPC470712
0.7037	Intermediate Similarity	NPC25946
0.703	Intermediate Similarity	NPC477895
0.7019	Intermediate Similarity	NPC474093
0.7019	Intermediate Similarity	NPC104910
0.701	Intermediate Similarity	NPC101399
0.701	Intermediate Similarity	NPC217822
0.701	Intermediate Similarity	NPC11847
0.701	Intermediate Similarity	NPC198938
0.699	Remote Similarity	NPC470718
0.697	Remote Similarity	NPC483767
0.697	Remote Similarity	NPC483769
0.697	Remote Similarity	NPC483768
0.697	Remote Similarity	NPC483766
0.6961	Remote Similarity	NPC217520
0.6907	Remote Similarity	NPC104883
0.6907	Remote Similarity	NPC488679
0.6903	Remote Similarity	NPC249560
0.6847	Remote Similarity	NPC473554
0.6733	Remote Similarity	NPC483765
0.6733	Remote Similarity	NPC81042
0.6667	Remote Similarity	NPC205824
0.6667	Remote Similarity	NPC487502
0.6593	Remote Similarity	NPC216496
0.6535	Remote Similarity	NPC36138
0.6518	Remote Similarity	NPC21359
0.6518	Remote Similarity	NPC460984
0.65	Remote Similarity	NPC603079
0.6452	Remote Similarity	NPC224530
0.6404	Remote Similarity	NPC231787
0.6364	Remote Similarity	NPC470125
0.6355	Remote Similarity	NPC139571
0.633	Remote Similarity	NPC470713
0.6321	Remote Similarity	NPC164704
0.63	Remote Similarity	NPC12013
0.63	Remote Similarity	NPC11432
0.63	Remote Similarity	NPC477628
0.63	Remote Similarity	NPC477613
0.6275	Remote Similarity	NPC477629
0.6121	Remote Similarity	NPC275977
0.6117	Remote Similarity	NPC89127
0.6091	Remote Similarity	NPC488734
0.6091	Remote Similarity	NPC488735
0.6091	Remote Similarity	NPC488739
0.6091	Remote Similarity	NPC488732
0.6091	Remote Similarity	NPC488738
0.6058	Remote Similarity	NPC292929
0.6058	Remote Similarity	NPC221342
0.6058	Remote Similarity	NPC476470
0.6036	Remote Similarity	NPC480445
0.6019	Remote Similarity	NPC97119
0.6019	Remote Similarity	NPC470715
0.6018	Remote Similarity	NPC241781
0.6017	Remote Similarity	NPC30011
0.6017	Remote Similarity	NPC72554
0.6	Remote Similarity	NPC602448
0.5984	Remote Similarity	NPC475179
0.5984	Remote Similarity	NPC487501
0.5982	Remote Similarity	NPC156785
0.5982	Remote Similarity	NPC474522
0.5981	Remote Similarity	NPC470416
0.5941	Remote Similarity	NPC129264
0.5938	Remote Similarity	NPC259957
0.5926	Remote Similarity	NPC173837
0.5882	Remote Similarity	NPC61904
0.5877	Remote Similarity	NPC488737
0.582	Remote Similarity	NPC97817
0.5772	Remote Similarity	NPC487500
0.5769	Remote Similarity	NPC122467
0.5769	Remote Similarity	NPC139060
0.5728	Remote Similarity	NPC472992
0.5702	Remote Similarity	NPC488740
0.5702	Remote Similarity	NPC488736
0.5702	Remote Similarity	NPC488733
0.5702	Remote Similarity	NPC470717
0.5686	Remote Similarity	NPC304741
0.567	Remote Similarity	NPC48093
0.5657	Remote Similarity	NPC170052
0.5657	Remote Similarity	NPC476215
0.5657	Remote Similarity	NPC135846
0.5652	Remote Similarity	NPC480444
0.5652	Remote Similarity	NPC470720
0.56	Remote Similarity	NPC116864
0.56	Remote Similarity	NPC244776
0.5596	Remote Similarity	NPC89052
0.5579	Remote Similarity	NPC104677
0.5577	Remote Similarity	NPC296018
0.5566	Remote Similarity	NPC472991
0.5547	Remote Similarity	NPC33083
0.5514	Remote Similarity	NPC80068
0.551	Remote Similarity	NPC159579
0.549	Remote Similarity	NPC471079
0.5481	Remote Similarity	NPC35167
0.5472	Remote Similarity	NPC270448
0.5437	Remote Similarity	NPC173582
0.5437	Remote Similarity	NPC470405
0.5437	Remote Similarity	NPC265885
0.5437	Remote Similarity	NPC181465
0.5437	Remote Similarity	NPC215710
0.5437	Remote Similarity	NPC163242
0.5437	Remote Similarity	NPC272068
0.5437	Remote Similarity	NPC473438
0.5437	Remote Similarity	NPC253788
0.5429	Remote Similarity	NPC253521
0.5429	Remote Similarity	NPC153755
0.5429	Remote Similarity	NPC113836
0.5426	Remote Similarity	NPC288084
0.5421	Remote Similarity	NPC270675
0.5421	Remote Similarity	NPC195685
0.5354	Remote Similarity	NPC129217
0.5333	Remote Similarity	NPC144097
0.5319	Remote Similarity	NPC54802
0.5319	Remote Similarity	NPC197304
0.5312	Remote Similarity	NPC111929
0.5312	Remote Similarity	NPC320283
0.5312	Remote Similarity	NPC41121
0.531	Remote Similarity	NPC303694
0.53	Remote Similarity	NPC85707
0.5259	Remote Similarity	NPC295625
0.5258	Remote Similarity	NPC77672
0.5258	Remote Similarity	NPC133671
0.5258	Remote Similarity	NPC135391
0.5258	Remote Similarity	NPC78263
0.5258	Remote Similarity	NPC250069
0.5234	Remote Similarity	NPC297503
0.5192	Remote Similarity	NPC258044
0.5192	Remote Similarity	NPC217387
0.5189	Remote Similarity	NPC255157
0.5189	Remote Similarity	NPC259896
0.5169	Remote Similarity	NPC470719
0.5146	Remote Similarity	NPC254855
0.5146	Remote Similarity	NPC94610
0.5146	Remote Similarity	NPC95866
0.514	Remote Similarity	NPC154741
0.5138	Remote Similarity	NPC142142
0.5135	Remote Similarity	NPC472994
0.5122	Remote Similarity	NPC487499
0.5091	Remote Similarity	NPC471669
0.5088	Remote Similarity	NPC473278
0.5086	Remote Similarity	NPC470716
0.5083	Remote Similarity	NPC209550
0.5052	Remote Similarity	NPC138915
0.505	Remote Similarity	NPC175107
0.5048	Remote Similarity	NPC609888
0.5046	Remote Similarity	NPC37668
0.5044	Remote Similarity	NPC599948
0.5041	Remote Similarity	NPC192539
0.5041	Remote Similarity	NPC480470

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC218161 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4209
0.1-0.2	4876
0.2-0.3	56
0.3-0.4	8
0.4-0.5	1
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