NPASS Compound

Natural Product: NPC140932

Natural Product ID	NPC140932
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	STHRNDDZYFUIDO-XOEGDGRGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 5.4365 -2.2430 -1.7621 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0567 -1.2464 -0.6463 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9262 -1.5661 0.5075 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1952 0.0972 -1.2556 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7546 1.1520 -0.3292 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6306 0.8243 0.6222 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7699 2.0817 0.6284 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5938 1.9795 -0.2997 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7086 0.8851 0.2417 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4725 1.1509 1.6977 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4814 -0.3674 0.0120 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9368 -1.4402 -0.5648 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4670 -1.5216 -1.0406 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2195 -0.4896 -0.2599 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7203 -0.5790 -0.4059 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1566 -0.4364 -1.8188 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1422 -1.9519 0.0693 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6009 -2.1156 0.3002 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 -0.8887 0.4304 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7017 0.3238 0.8982 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4970 1.5319 0.3730 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9032 0.4033 2.4243 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2592 0.4293 0.5413 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8958 1.8126 0.0157 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4623 2.0165 -0.2511 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6220 0.8395 -0.5327 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1441 0.9372 -1.9962 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4490 -1.1783 1.3554 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9065 -0.4275 0.4343 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5816 -1.4602 -0.4364 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2331 0.8490 1.9903 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3871 1.1342 2.1778 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9542 -1.9769 -2.7124 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0911 -3.2461 -1.3901 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5396 -2.3089 -1.8319 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6974 -0.7573 0.6743 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3608 -1.7685 1.4646 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5459 -2.4947 0.3689 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2332 0.3101 -1.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5477 0.1232 -2.1584 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6782 1.5207 0.2153 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5172 2.0469 -0.9856 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3925 2.3392 1.6377 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3406 2.9777 0.3010 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9717 1.8067 -1.3056 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0495 2.9248 -0.2603 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4532 0.7007 2.1089 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4081 2.2283 1.9698 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2865 0.7538 2.3440 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5592 -2.3115 -0.6867 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8481 -2.5611 -0.9161 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5238 -1.3434 -2.1562 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0441 -0.7534 0.8249 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1704 -0.9046 -1.9991 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2563 0.5900 -2.1865 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4914 -1.0501 -2.4605 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8454 -2.7576 -0.6664 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5193 -2.1668 0.9775 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7090 -2.7719 1.2153 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0811 -2.7414 -0.5100 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0054 -0.6441 -0.5024 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5008 1.5835 -0.7157 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5634 1.2868 0.6617 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2619 2.4532 0.9063 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9317 0.6569 2.6845 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5478 -0.5526 2.8873 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2215 1.1950 2.7990 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6952 0.3412 1.4959 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5397 2.1050 -0.8524 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2316 2.5149 0.8375 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0036 2.6007 0.5901 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4004 2.7642 -1.1026 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9301 0.7451 -2.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7847 0.4009 -2.1755 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1120 2.0335 -2.1103 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7701 -2.1172 1.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8199 -0.9698 1.4344 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1640 -1.4417 -1.4750 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4676 -2.5018 -0.0821 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6062 0.6026 2.8233 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 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 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 19 28 1 0 11 29 1 0 29 30 1 0 6 31 1 1 31 32 2 0 30 2 1 0 29 6 1 0 26 9 1 0 26 14 1 0 23 15 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 7 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 10 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 1 16 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 18 59 1 0 18 60 1 0 19 61 1 6 21 62 1 0 21 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 1 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 27 73 1 0 27 74 1 0 27 75 1 0 28 76 1 0 29 77 1 1 30 78 1 0 30 79 1 0 31 80 1 0 M END

Standard InCHIKey	STHRNDDZYFUIDO-XOEGDGRGSA-N
Standard InCHI	InChI=1S/C30H48O2/c1-25(2)14-16-30(19-31)17-15-28(6)20(21(30)18-25)8-9-23-27(5)12-11-24(32)26(3,4)22(27)10-13-29(23,28)7/h8,19,21-24,32H,9-18H2,1-7H3/t21-,22+,23-,24-,27+,28-,29-,30+/m1/s1
SMILES	CC1(C)CC[C@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@H]2C1)C=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.37	Volume:	496.961 ? Van der Waals volume.
Dense:	0.886	LogP:	5.889 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.642 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.342 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
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:	0.342	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.812	Fsp³:	0.9
MCE-18:	102.667 ? 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:	0.943	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.723	Promiscuous compounds:	0.041

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.213	MDCK Permeability:	-4.922
Pgp-inhibitor:	0.897	Pgp-substrate:	0.017
PAMPA:	0.925 ? 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%):	0.086	30% Bioavailability (F30%):	0.017
50% Bioavailability (F50%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232	MRP1:	0.306
Plasma Protein Binding (PPB):	92.115%	Volume Distribution (VD):	0.101
Fu:	9.212% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.981	BCRP inhibitor:	0.793
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.096	CYP1A2-substrate:	0.784
CYP2C19-inhibitor:	0.993	CYP2C19-substrate:	0.988
CYP2C9-inhibitor:	0.052	CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.489	CYP2D6-substrate:	0.636
CYP3A4-inhibitor:	0.941	CYP3A4-substrate:	0.8
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.995 ? 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):

8.796

Half-life (T1/2):

0.528

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.086
Human Hepatotoxicity (H-HT):	0.514	Drug-induced Liver Injury (DILI):	0.053
AMES Toxicity:	0.464	Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.614	Skin Sensitization:	0.763
Carcinogencity:	0.916	Eye Corrosion:	0.028
Eye Irritation:	0.523	Respiratory Toxicity:	0.754
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.511
Hematotoxicity:	0.559	Drug-induced Nephrotoxicity:	0.808
Genotoxicity:	0.713	RPMI-8226 Immunitoxicity:	0.07
A549 Cytotoxicity:	0.27	Hek293 Cytotoxicity:	0.385
BCF:	1.936 ? 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:	4.212 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.586 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.032 ? 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]
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]
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]
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]
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]
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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC140932 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	20190
0.1-0.2	24372
0.2-0.3	3966
0.3-0.4	991
0.4-0.5	229
0.5-0.6	73
0.6-0.7	26
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC235341
0.8113	Intermediate Similarity	NPC290598
0.8113	Intermediate Similarity	NPC30590
0.7759	Intermediate Similarity	NPC246708
0.7679	Intermediate Similarity	NPC101475
0.7241	Intermediate Similarity	NPC253807
0.7241	Intermediate Similarity	NPC158662
0.7119	Intermediate Similarity	NPC95594
0.7069	Intermediate Similarity	NPC34177
0.6833	Remote Similarity	NPC470588
0.6825	Remote Similarity	NPC488519
0.678	Remote Similarity	NPC196753
0.6557	Remote Similarity	NPC224145
0.65	Remote Similarity	NPC311078
0.6333	Remote Similarity	NPC474989
0.6271	Remote Similarity	NPC27765
0.6271	Remote Similarity	NPC122418
0.6271	Remote Similarity	NPC491014
0.6164	Remote Similarity	NPC167383
0.6129	Remote Similarity	NPC475862
0.6129	Remote Similarity	NPC480924
0.6119	Remote Similarity	NPC49776
0.6119	Remote Similarity	NPC63118
0.6119	Remote Similarity	NPC474436
0.6061	Remote Similarity	NPC7260
0.6061	Remote Similarity	NPC210037
0.6061	Remote Similarity	NPC120968
0.6061	Remote Similarity	NPC171203
0.6061	Remote Similarity	NPC307426
0.6061	Remote Similarity	NPC98442
0.6061	Remote Similarity	NPC242468
0.6061	Remote Similarity	NPC227467
0.6061	Remote Similarity	NPC273621
0.6	Remote Similarity	NPC477579
0.6	Remote Similarity	NPC601696
0.5942	Remote Similarity	NPC294360
0.5909	Remote Similarity	NPC480946
0.5909	Remote Similarity	NPC213412
0.5909	Remote Similarity	NPC130577
0.5909	Remote Similarity	NPC142415
0.5909	Remote Similarity	NPC102683
0.5909	Remote Similarity	NPC136313
0.5909	Remote Similarity	NPC2539
0.5873	Remote Similarity	NPC195334
0.5846	Remote Similarity	NPC40552
0.5781	Remote Similarity	NPC230295
0.5781	Remote Similarity	NPC159168
0.5781	Remote Similarity	NPC98386
0.5738	Remote Similarity	NPC120098
0.5692	Remote Similarity	NPC480950
0.5672	Remote Similarity	NPC191965
0.5672	Remote Similarity	NPC610937
0.5652	Remote Similarity	NPC164349
0.5645	Remote Similarity	NPC142754
0.5625	Remote Similarity	NPC40394
0.5588	Remote Similarity	NPC112866
0.5538	Remote Similarity	NPC238992
0.5538	Remote Similarity	NPC3915
0.5522	Remote Similarity	NPC477872
0.5507	Remote Similarity	NPC18872
0.5507	Remote Similarity	NPC290614
0.5441	Remote Similarity	NPC187722
0.5441	Remote Similarity	NPC10005
0.5441	Remote Similarity	NPC214756
0.5441	Remote Similarity	NPC91525
0.5441	Remote Similarity	NPC172361
0.5429	Remote Similarity	NPC228784
0.5429	Remote Similarity	NPC324341
0.5429	Remote Similarity	NPC298554
0.5429	Remote Similarity	NPC601810
0.5385	Remote Similarity	NPC291379
0.5385	Remote Similarity	NPC237503
0.5385	Remote Similarity	NPC478657
0.5362	Remote Similarity	NPC182797
0.5362	Remote Similarity	NPC51700
0.5362	Remote Similarity	NPC88716
0.5362	Remote Similarity	NPC68160
0.5362	Remote Similarity	NPC52169
0.5362	Remote Similarity	NPC488562
0.5362	Remote Similarity	NPC606443
0.5352	Remote Similarity	NPC480919
0.5303	Remote Similarity	NPC53744
0.5294	Remote Similarity	NPC162107
0.5294	Remote Similarity	NPC46912
0.527	Remote Similarity	NPC86368
0.527	Remote Similarity	NPC283343
0.5231	Remote Similarity	NPC132478
0.5231	Remote Similarity	NPC237344
0.5224	Remote Similarity	NPC133954
0.5224	Remote Similarity	NPC470224
0.5224	Remote Similarity	NPC267517
0.5217	Remote Similarity	NPC198664
0.5211	Remote Similarity	NPC202728
0.5211	Remote Similarity	NPC158059
0.5211	Remote Similarity	NPC293564
0.5205	Remote Similarity	NPC488520
0.52	Remote Similarity	NPC473160
0.5143	Remote Similarity	NPC286786
0.5143	Remote Similarity	NPC195019
0.5143	Remote Similarity	NPC481361
0.5139	Remote Similarity	NPC263393
0.5135	Remote Similarity	NPC175006
0.5132	Remote Similarity	NPC480920
0.5075	Remote Similarity	NPC328052
0.5067	Remote Similarity	NPC471433
0.5067	Remote Similarity	NPC273668
0.5067	Remote Similarity	NPC471432
0.5067	Remote Similarity	NPC488522

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC140932 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7214
0.1-0.2	1860
0.2-0.3	72
0.3-0.4	2
0.4-0.5	1
0.5-0.6	1
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
0.5821	Remote Similarity	NPD7645	Phase 2

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