NPASS Compound

Natural Product: NPC114743

Natural Product ID	NPC114743
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YWPLTMNXKKXXII-CYWJYPAKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL565135
PubChem CID	14314564
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 82 86 0 0 0 0 0 0 0 0999 V2000 6.6128 -1.1582 -2.7251 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1433 -0.9863 -1.3773 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9720 0.0477 -0.7734 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4853 1.1530 -0.3104 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1996 1.7284 -0.1998 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8988 1.0905 -0.3044 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5251 0.0445 0.7147 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1832 -0.5435 0.4660 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9257 -1.6101 1.5235 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4852 -1.5057 1.9205 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1028 -0.8101 0.7085 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9678 0.2736 0.4479 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7807 1.3047 1.4970 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5716 0.8791 -0.8736 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8371 0.8171 -1.2619 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8621 0.5674 -0.2192 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4414 -0.2062 0.9569 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3799 -1.2972 1.3996 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8233 -0.7910 1.4095 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1403 -0.4919 -0.0424 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2560 0.5402 -0.6267 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8521 1.7301 0.1217 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6476 0.7381 -2.0786 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8538 -0.0918 -2.4605 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9819 0.3017 -1.5300 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5995 -0.1437 -0.1213 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9677 0.9878 0.8119 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4551 -1.3552 0.1879 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2066 -0.1859 -1.9235 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1569 -1.8272 -0.3916 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6884 0.5768 2.1339 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4479 -0.2156 -0.7003 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8572 -1.2925 -1.1588 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3071 0.6865 -0.1543 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2899 -1.8705 -2.7744 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0951 -0.8542 -1.4856 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4316 -1.9624 -0.8867 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3179 1.8188 0.1087 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1354 2.6284 -0.9572 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1259 2.3827 0.7694 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1424 1.9666 -0.2006 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6702 0.7706 -1.3377 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2428 -0.7678 0.6424 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2667 -1.0783 -0.5086 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6271 -1.5637 2.3749 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1125 -2.6383 1.0822 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0136 -2.5329 1.9166 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2766 -1.0367 2.8733 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4719 0.9346 2.4968 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1091 1.9338 1.1778 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5899 2.0603 1.5655 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2381 0.4384 -1.6463 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8575 1.9722 -0.8189 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1493 1.7715 -1.7916 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9814 0.0553 -2.0855 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3885 0.4973 1.8325 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2862 -2.2440 0.8790 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1552 -1.5169 2.4852 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4502 -1.6265 1.7240 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8643 0.0992 2.0520 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9873 -1.4467 -0.5941 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6527 2.6831 -0.4100 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1855 1.8239 1.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9411 1.7991 -2.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8439 0.5155 -2.7823 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1558 0.2362 -3.4762 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6631 -1.1624 -2.4975 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0265 1.4291 -1.5704 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7830 0.7677 1.8646 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0629 1.1564 0.7009 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4768 1.9020 0.4354 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2086 -2.1904 -0.4770 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4491 -1.6104 1.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5214 -1.0703 -0.0419 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9399 0.4483 -1.6654 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1077 -2.8676 -0.0373 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1971 -1.9610 -0.8113 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4785 -1.6400 -1.2540 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5119 0.0821 2.6907 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9263 1.6611 2.1618 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7751 0.3654 2.7666 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2869 0.4866 0.0757 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 1 0 16 15 1 6 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 25 29 1 0 11 30 1 6 7 31 1 0 3 32 1 0 32 33 2 0 32 34 1 0 12 8 1 0 22 16 1 0 17 11 1 0 26 20 1 0 21 16 1 0 1 35 1 0 2 36 1 0 2 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 7 43 1 1 8 44 1 6 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 13 49 1 0 13 50 1 0 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 17 56 1 1 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 6 22 62 1 0 22 63 1 0 23 64 1 0 23 65 1 0 24 66 1 0 24 67 1 0 25 68 1 1 27 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 31 80 1 0 31 81 1 0 34 82 1 0 M END

Standard InCHIKey	YWPLTMNXKKXXII-CYWJYPAKSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-19(7-6-8-20(17-31)25(33)34)21-11-13-28(5)23-10-9-22-26(2,3)24(32)12-14-29(22)18-30(23,29)16-15-27(21,28)4/h8,19,21-24,31-32H,6-7,9-18H2,1-5H3,(H,33,34)/b20-8+/t19-,21-,22+,23+,24-,27-,28+,29-,30+/m1/s1
SMILES	OC/C(=CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@H](C2(C)C)O)C)C)/C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	3.573 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.232 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.236 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.402	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.574	Fsp³:	0.9
MCE-18:	134.368 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.557	Fluc inhibitor:	0.018 ? 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:	0.427	Promiscuous compounds:	0.166

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.385	MDCK Permeability:	-4.995
Pgp-inhibitor:	0.031	Pgp-substrate:	0.004
PAMPA:	0.916 ? 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):	0.019
20% Bioavailability (F20%):	0.598	30% Bioavailability (F30%):	0.624
50% Bioavailability (F50%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039	MRP1:	0.351
Plasma Protein Binding (PPB):	86.928%	Volume Distribution (VD):	-0.516
Fu:	12.826% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.498
BSEP inhibitor:	0.911

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.029
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):

8.648

Half-life (T1/2):

0.89

ADMET: Toxicity

hERG Blockers:	0.048	hERG Blockers (10um):	0.067
Human Hepatotoxicity (H-HT):	0.742	Drug-induced Liver Injury (DILI):	0.125
AMES Toxicity:	0.229	Rat Oral Acute Toxicity:	0.215
Maximum Recommended Daily Dose:	0.388	Skin Sensitization:	0.965
Carcinogencity:	0.64	Eye Corrosion:	0.0
Eye Irritation:	0.173	Respiratory Toxicity:	0.911
Drug-induced Neurotoxicity:	0.014	Ototoxicity:	0.783
Hematotoxicity:	0.456	Drug-induced Nephrotoxicity:	0.585
Genotoxicity:	0.833	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.205	Hek293 Cytotoxicity:	0.16
BCF:	1.642 ? 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:	4.494 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.828 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.274 ? 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]
NPO41067	Trigona minor	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28783356]
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
IC50	4
CD100	1
PC50	2

Activity Type	# Activity
Cell line	3
Individual protein	2
Single protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT946	Individual protein	ATP-citrate synthase	Homo sapiens	IC50	=	11400.0	nM	PMID[37291059]
NPT30007	Single protein	Acetyl-CoA carboxylase 1	Homo sapiens	IC50	=	8400.0	nM	PMID[37291059]

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	=	25.0	uM	PMID[19572611]
NPT461	Cell line	PANC-1	Homo sapiens	PC50	=	15.5	uM	PMID[19572611]
NPT461	Cell line	PANC-1	Homo sapiens	PC50	=	3.7	uM	PMID[28783356]

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 NPC114743 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	22295
0.1-0.2	23766
0.2-0.3	3162
0.3-0.4	481
0.4-0.5	90
0.5-0.6	34
0.6-0.7	18
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC195366
0.8545	High Similarity	NPC110923
0.8545	High Similarity	NPC74296
0.7419	Intermediate Similarity	NPC156546
0.7258	Intermediate Similarity	NPC23217
0.7049	Intermediate Similarity	NPC85379
0.7049	Intermediate Similarity	NPC144909
0.7049	Intermediate Similarity	NPC476304
0.7	Intermediate Similarity	NPC476186
0.6667	Remote Similarity	NPC85346
0.6667	Remote Similarity	NPC65897
0.6667	Remote Similarity	NPC80237
0.6613	Remote Similarity	NPC483817
0.6508	Remote Similarity	NPC479654
0.6508	Remote Similarity	NPC479656
0.6462	Remote Similarity	NPC29152
0.6393	Remote Similarity	NPC89747
0.614	Remote Similarity	NPC41577
0.6066	Remote Similarity	NPC472341
0.6061	Remote Similarity	NPC117122
0.6034	Remote Similarity	NPC299948
0.6034	Remote Similarity	NPC241085
0.6034	Remote Similarity	NPC607543
0.6	Remote Similarity	NPC470830
0.6	Remote Similarity	NPC195530
0.6	Remote Similarity	NPC479659
0.6	Remote Similarity	NPC273366
0.5932	Remote Similarity	NPC331618
0.5932	Remote Similarity	NPC257191
0.5932	Remote Similarity	NPC196358
0.5902	Remote Similarity	NPC22133
0.5846	Remote Similarity	NPC16287
0.5846	Remote Similarity	NPC236618
0.5833	Remote Similarity	NPC200243
0.5833	Remote Similarity	NPC254509
0.5833	Remote Similarity	NPC82623
0.5833	Remote Similarity	NPC604180
0.5806	Remote Similarity	NPC76518
0.5738	Remote Similarity	NPC472342
0.5735	Remote Similarity	NPC66344
0.5672	Remote Similarity	NPC181743
0.5672	Remote Similarity	NPC186975
0.5672	Remote Similarity	NPC178025
0.5625	Remote Similarity	NPC473238
0.5625	Remote Similarity	NPC134481
0.5455	Remote Similarity	NPC18384
0.5312	Remote Similarity	NPC67872
0.5286	Remote Similarity	NPC194937
0.5286	Remote Similarity	NPC146937
0.5286	Remote Similarity	NPC476038
0.5286	Remote Similarity	NPC479653
0.527	Remote Similarity	NPC470113
0.5231	Remote Similarity	NPC12722
0.5156	Remote Similarity	NPC70982
0.5156	Remote Similarity	NPC473279
0.5156	Remote Similarity	NPC302041
0.5152	Remote Similarity	NPC606508
0.5139	Remote Similarity	NPC479657
0.507	Remote Similarity	NPC290969
0.507	Remote Similarity	NPC476174
0.5068	Remote Similarity	NPC486362

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC114743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6260
0.1-0.2	2798
0.2-0.3	83
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