NPASS Compound

Natural Product: NPC89747

Natural Product ID	NPC89747
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WQGJXPXTLGQILL-VGMYXFKYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL551129
PubChem CID	14314541
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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 80 84 0 0 0 0 0 0 0 0999 V2000 7.7151 -0.5389 1.3551 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7507 -1.0436 -0.0333 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8850 -0.5417 -0.8901 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9087 0.5091 -0.4302 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5505 -0.0529 -0.6590 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4382 0.9177 -0.2304 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6071 2.1505 -1.0428 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1665 0.1741 -0.4274 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2562 -1.0684 0.4724 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9187 -1.2478 1.1046 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0186 -0.4168 0.2332 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2245 -1.1450 -1.0403 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2240 0.0555 0.9259 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9846 -1.0154 1.6325 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0798 -1.6525 0.8871 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8734 -0.7829 -0.0090 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3492 -0.6742 0.4008 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8198 -2.1097 0.6072 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5267 0.0508 1.6904 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1404 -0.0697 -0.7051 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5307 1.0416 -1.4411 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0379 1.0235 -1.5745 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3838 0.5697 -0.2610 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1542 1.6346 0.6958 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9994 0.9053 0.0059 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2501 1.5528 -1.0936 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2062 1.6604 -0.9965 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9086 0.8164 0.0066 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0400 1.6101 1.2821 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3632 0.3687 -0.1586 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6904 -2.0581 -0.4854 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5442 -2.5853 0.2644 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9917 0.5347 1.3884 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7556 -0.7355 1.8638 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4995 -1.0815 1.9261 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8497 -0.8594 -1.9196 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1146 1.3810 -1.1188 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0795 0.7603 0.6179 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4336 -0.2542 -1.7607 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4690 -1.0167 -0.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6758 1.1545 0.8295 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5683 2.6339 -0.6959 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6890 1.9593 -2.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8414 2.9277 -0.8902 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1119 -0.1276 -1.4896 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6072 -1.9475 -0.1041 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9964 -0.9101 1.2892 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6003 -2.3216 1.0060 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8647 -1.0126 2.1716 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3190 -1.2775 -1.2815 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1656 -2.2039 -0.9855 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2067 -0.6752 -1.9441 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8593 0.7392 1.7557 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3901 -0.6619 2.6273 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2294 -1.8028 1.9316 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6574 -2.5648 0.3662 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8003 -2.1072 1.6326 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9359 -1.3234 -1.0053 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8259 -2.3946 1.6749 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1699 -2.8295 0.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8486 -2.2665 0.2255 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6339 1.1394 1.4996 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7937 -0.1919 2.4576 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5290 -0.2638 2.1074 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4288 -0.9057 -1.4063 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8054 2.0346 -0.9808 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9531 1.0847 -2.4701 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6820 2.0479 -1.8121 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7083 0.3547 -2.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2830 1.5462 1.7824 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2134 2.7000 0.3531 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7267 2.5653 -1.2657 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5058 0.9977 -2.0459 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6989 1.4728 -1.9948 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4618 2.7390 -0.7755 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9913 2.2186 1.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1125 1.0109 2.1882 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2372 2.3907 1.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0606 -0.3031 -0.2191 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6744 -2.3923 -1.5115 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 23 22 1 6 23 24 1 0 25 24 1 1 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 20 30 1 0 2 31 1 0 31 32 2 0 28 8 1 0 28 11 1 0 25 13 1 0 23 16 1 0 25 23 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 6 41 1 1 7 42 1 0 7 43 1 0 7 44 1 0 8 45 1 6 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 12 51 1 0 12 52 1 0 13 53 1 1 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 16 58 1 6 18 59 1 0 18 60 1 0 18 61 1 0 19 62 1 0 19 63 1 0 19 64 1 0 20 65 1 6 21 66 1 0 21 67 1 0 22 68 1 0 22 69 1 0 24 70 1 0 24 71 1 0 26 72 1 0 26 73 1 0 27 74 1 0 27 75 1 0 29 76 1 0 29 77 1 0 29 78 1 0 30 79 1 0 31 80 1 0 M END

Standard InCHIKey	WQGJXPXTLGQILL-VGMYXFKYSA-N
Standard InCHI	InChI=1S/C30H48O2/c1-20(18-31)8-7-9-21(2)22-12-14-28(6)24-11-10-23-26(3,4)25(32)13-15-29(23)19-30(24,29)17-16-27(22,28)5/h8,18,21-25,32H,7,9-17,19H2,1-6H3/b20-8+/t21-,22-,23+,24+,25+,27-,28+,29-,30+/m1/s1
SMILES	C/C(=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@H](CC[C@]54C[C@@]35CC[C@]12C)O)/C=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.37	Volume:	496.961 ? Van der Waals volume.
Dense:	0.886	LogP:	4.733 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.886 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.786 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.358	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.549	Fsp³:	0.9
MCE-18:	130.737 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.82	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.638	Promiscuous compounds:	0.116

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.214	MDCK Permeability:	-4.97
Pgp-inhibitor:	0.415	Pgp-substrate:	0.024
PAMPA:	0.19 ? 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%):	0.104	30% Bioavailability (F30%):	0.443
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11	MRP1:	0.069
Plasma Protein Binding (PPB):	95.183%	Volume Distribution (VD):	-0.291
Fu:	5.189% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.974
BSEP inhibitor:	0.703

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.438
CYP2C19-inhibitor:	0.996	CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.237
CYP2D6-inhibitor:	0.436	CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.974
HLM stability:	0.993 ? 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):

16.515

Half-life (T1/2):

0.909

ADMET: Toxicity

hERG Blockers:	0.081	hERG Blockers (10um):	0.276
Human Hepatotoxicity (H-HT):	0.485	Drug-induced Liver Injury (DILI):	0.022
AMES Toxicity:	0.481	Rat Oral Acute Toxicity:	0.256
Maximum Recommended Daily Dose:	0.761	Skin Sensitization:	0.811
Carcinogencity:	0.783	Eye Corrosion:	0.004
Eye Irritation:	0.544	Respiratory Toxicity:	0.879
Drug-induced Neurotoxicity:	0.035	Ototoxicity:	0.371
Hematotoxicity:	0.259	Drug-induced Nephrotoxicity:	0.389
Genotoxicity:	0.487	RPMI-8226 Immunitoxicity:	0.094
A549 Cytotoxicity:	0.283	Hek293 Cytotoxicity:	0.342
BCF:	2.48 ? 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:	5.342 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.399 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.152 ? 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
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757720]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593279]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309313]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17716892]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	China	n.a.	PMID[19278239]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	leaves	Kibale National Park, Uganda	2000-2001	PMID[19299148]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	Ywar Taw village, Shan State of Myanmar	2006-Dec	PMID[19572611]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25211032]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117521]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31873014]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29363	Aconitum nevadense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28784	Alseodaphne corneri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27269	Annona impressivenia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29510	Aulacocephalus temmincki	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28971	Bersama yangambiensis	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29189	Castanopsis sclerophylla	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29400	Conocephalum japonicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26192	Cordylanthus kingii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25981	Crinipellis scabella	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29127	Cystophora scalaris	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29047	Disynaphia halimifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4244	Doodia picta	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28845	Eragrostis viscosa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1245	Eunicella cavolinii	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28824	Forsteronia refracta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3340	Fridericia chica	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28898	Grewia mollis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29203	Gymnocarpium robertianum	Species	Cystopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29154	Heliotropium floridum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28937	Heterotheca grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29415	Hovenia acerba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29142	Kaunia saltensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13818	Narcissus concolor	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29225	Oncoba echinata	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28918	Ophiolepis superba	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29068	Papilio phorcas	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3744	Polycephalomyces nipponicus	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9157	Rubrivivax gelatinosus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29242	Salvia dorrii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29488	Sophora angustifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29446	Stevia polycephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29292	Teucrium depressum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29242	Salvia dorrii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29225	Oncoba echinata	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29363	Aconitum nevadense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26192	Cordylanthus kingii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27269	Annona impressivenia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29415	Hovenia acerba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29203	Gymnocarpium robertianum	Species	Cystopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3340	Fridericia chica	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1245	Eunicella cavolinii	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29127	Cystophora scalaris	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28898	Grewia mollis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29400	Conocephalum japonicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29446	Stevia polycephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28918	Ophiolepis superba	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29047	Disynaphia halimifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28971	Bersama yangambiensis	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13818	Narcissus concolor	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28784	Alseodaphne corneri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4244	Doodia picta	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29142	Kaunia saltensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28937	Heterotheca grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28845	Eragrostis viscosa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28824	Forsteronia refracta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29510	Aulacocephalus temmincki	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29154	Heliotropium floridum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29292	Teucrium depressum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29189	Castanopsis sclerophylla	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25981	Crinipellis scabella	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3744	Polycephalomyces nipponicus	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9157	Rubrivivax gelatinosus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29488	Sophora angustifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29068	Papilio phorcas	Species	Papilionidae	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
CD100	1
PC50	1

Activity Type	# Activity
Cell line	2

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
NPT461	Cell line	PANC-1	Homo sapiens	CD100	>	100.0	uM	PMID[19572611]
NPT461	Cell line	PANC-1	Homo sapiens	PC50	>	100.0	uM	PMID[19572611]

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 NPC89747 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	19211
0.1-0.2	25726
0.2-0.3	4281
0.3-0.4	461
0.4-0.5	115
0.5-0.6	26
0.6-0.7	30
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.82	Intermediate Similarity	NPC85346
0.82	Intermediate Similarity	NPC65897
0.82	Intermediate Similarity	NPC80237
0.6981	Remote Similarity	NPC331618
0.6981	Remote Similarity	NPC257191
0.6852	Remote Similarity	NPC604180
0.6792	Remote Similarity	NPC607543
0.6786	Remote Similarity	NPC76518
0.6727	Remote Similarity	NPC273366
0.6667	Remote Similarity	NPC196358
0.661	Remote Similarity	NPC110923
0.661	Remote Similarity	NPC74296
0.6607	Remote Similarity	NPC22133
0.6604	Remote Similarity	NPC41577
0.6545	Remote Similarity	NPC200243
0.6545	Remote Similarity	NPC254509
0.6545	Remote Similarity	NPC82623
0.6481	Remote Similarity	NPC299948
0.6481	Remote Similarity	NPC241085
0.6429	Remote Similarity	NPC472342
0.6429	Remote Similarity	NPC195530
0.6406	Remote Similarity	NPC476187
0.6393	Remote Similarity	NPC195366
0.6393	Remote Similarity	NPC114743
0.6333	Remote Similarity	NPC18384
0.6316	Remote Similarity	NPC302041
0.6207	Remote Similarity	NPC472341
0.614	Remote Similarity	NPC470830
0.614	Remote Similarity	NPC479659
0.6102	Remote Similarity	NPC12722
0.6	Remote Similarity	NPC473238
0.6	Remote Similarity	NPC134481
0.6	Remote Similarity	NPC606508
0.5968	Remote Similarity	NPC483817
0.5932	Remote Similarity	NPC67872
0.5932	Remote Similarity	NPC113978
0.5714	Remote Similarity	NPC307776
0.5625	Remote Similarity	NPC85379
0.5625	Remote Similarity	NPC144909
0.5625	Remote Similarity	NPC476304
0.5593	Remote Similarity	NPC214770
0.5593	Remote Similarity	NPC477856
0.5574	Remote Similarity	NPC139206
0.5556	Remote Similarity	NPC476186
0.5538	Remote Similarity	NPC475772
0.55	Remote Similarity	NPC70982
0.55	Remote Similarity	NPC473279
0.5455	Remote Similarity	NPC102426
0.5455	Remote Similarity	NPC283733
0.541	Remote Similarity	NPC269058
0.541	Remote Similarity	NPC71520
0.5373	Remote Similarity	NPC191684
0.5323	Remote Similarity	NPC477858
0.5217	Remote Similarity	NPC603266
0.5211	Remote Similarity	NPC470906
0.5211	Remote Similarity	NPC603020
0.5147	Remote Similarity	NPC300179
0.5082	Remote Similarity	NPC240604
0.5082	Remote Similarity	NPC145552

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC89747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7276
0.1-0.2	1804
0.2-0.3	69
0.3-0.4	1
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