NPASS Compound

Natural Product: NPC22133

Natural Product ID	NPC22133
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WNTCMDLOMSFFPE-GXBJFGSMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL523455
PubChem CID	21626061
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 77 81 0 0 0 0 0 0 0 0999 V2000 7.1660 1.4348 1.7629 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5389 0.1301 1.4913 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4774 -0.7061 2.4287 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0068 -0.1739 0.1670 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4569 -1.3498 -0.0280 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9063 -1.7028 -1.3461 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4187 -2.0233 -1.2901 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6235 -0.8559 -0.7862 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8114 0.3698 -1.6827 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6082 1.2351 -1.3802 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7393 0.4367 -0.4326 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1454 -0.9916 -0.8405 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6693 -1.2184 -2.2576 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4994 -1.9289 0.0925 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7357 -1.4346 0.7913 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5143 -0.4185 0.0314 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7180 0.5782 -0.7125 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1415 2.0107 -0.4666 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6355 2.0674 -0.7765 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3072 1.3247 0.3580 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8280 -0.0634 0.5119 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8059 -0.9129 -0.6996 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3692 -0.6291 1.8112 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2898 0.3450 2.5035 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3655 0.8631 1.5788 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8047 1.3703 0.2672 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3196 2.7863 0.0740 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3555 0.5395 -0.8530 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2372 -0.2254 1.3478 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0968 0.7498 0.9821 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3201 -3.2091 -0.3507 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2734 1.2747 1.7384 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8490 1.8336 2.7578 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8607 2.1563 0.9865 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0838 0.5830 -0.6118 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4101 -2.0522 0.7753 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1534 -0.9884 -2.1370 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4014 -2.6723 -1.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1323 -2.3852 -2.2941 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9984 -0.5846 0.2043 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7551 0.9057 -1.4108 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8014 0.1271 -2.7446 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9286 2.1744 -0.8673 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0200 1.5272 -2.2465 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8365 -0.3788 -2.9303 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4148 -1.5251 -2.2205 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1713 -2.1030 -2.7039 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2544 -2.8656 -0.4966 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2026 -2.2532 0.8819 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4093 -2.3368 0.9099 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5437 -1.1209 1.8372 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8708 0.4101 -1.8074 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6511 2.6585 -1.2013 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0261 2.3437 0.5648 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0081 3.1194 -0.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8760 1.6562 -1.7595 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0327 1.8932 1.2937 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9825 -2.0074 -0.6490 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9650 -0.5020 -1.7177 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5458 -0.8557 2.5320 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9065 -1.5857 1.6487 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7552 1.1369 3.0453 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8317 -0.2549 3.2927 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9046 1.6589 2.1326 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9819 3.4447 0.9080 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4273 2.7266 0.1106 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0653 3.1948 -0.9251 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2410 -0.5357 -0.7311 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9535 0.8351 -1.8352 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4644 0.7366 -0.8763 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0720 0.0791 0.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5721 -0.0475 1.5485 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2402 1.1267 1.5940 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8242 1.6147 0.9913 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4924 -2.8614 0.7088 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1904 -3.8939 -0.5708 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4207 -3.8049 -0.4862 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 2 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 6 12 14 1 0 14 15 1 0 16 15 1 1 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 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 1 7 31 1 0 12 8 1 0 22 16 1 0 17 11 1 0 26 20 1 0 21 16 1 0 1 32 1 0 1 33 1 0 1 34 1 0 4 35 1 0 5 36 1 0 6 37 1 0 6 38 1 0 7 39 1 6 8 40 1 1 9 41 1 0 9 42 1 0 10 43 1 0 10 44 1 0 13 45 1 0 13 46 1 0 13 47 1 0 14 48 1 0 14 49 1 0 15 50 1 0 15 51 1 0 17 52 1 6 18 53 1 0 18 54 1 0 19 55 1 0 19 56 1 0 20 57 1 1 22 58 1 0 22 59 1 0 23 60 1 0 23 61 1 0 24 62 1 0 24 63 1 0 25 64 1 1 27 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 M END

Standard InCHIKey	WNTCMDLOMSFFPE-GXBJFGSMSA-N
Standard InCHI	InChI=1S/C29H46O2/c1-19(8-7-9-20(2)30)21-12-14-27(6)23-11-10-22-25(3,4)24(31)13-15-28(22)18-29(23,28)17-16-26(21,27)5/h7,9,19,21-24,31H,8,10-18H2,1-6H3/b9-7+/t19-,21-,22+,23+,24+,26-,27+,28-,29+/m1/s1
SMILES	CC(=O)/C=C/C[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

Calculated Properties

Physi-Chem Properties

Molecular Weight:	426.35	Volume:	479.665 ? Van der Waals volume.
Dense:	0.889	LogP:	3.932 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.623 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.224 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	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:	0.493	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.492	Fsp³:	0.897
MCE-18:	131.564 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.806	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.629	Promiscuous compounds:	0.313

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.199	MDCK Permeability:	-4.907
Pgp-inhibitor:	0.321	Pgp-substrate:	0.029
PAMPA:	0.21 ? 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%):	0.039	30% Bioavailability (F30%):	0.167
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204	MRP1:	0.102
Plasma Protein Binding (PPB):	94.868%	Volume Distribution (VD):	-0.132
Fu:	7.205% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.962
BSEP inhibitor:	0.943

ADMET: Metabolism

CYP1A2-inhibitor:	0.028	CYP1A2-substrate:	0.212
CYP2C19-inhibitor:	0.99	CYP2C19-substrate:	0.529
CYP2C9-inhibitor:	0.036	CYP2C9-substrate:	0.23
CYP2D6-inhibitor:	0.905	CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.987
HLM stability:	0.912 ? 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):

15.911

Half-life (T1/2):

0.809

ADMET: Toxicity

hERG Blockers:	0.097	hERG Blockers (10um):	0.286
Human Hepatotoxicity (H-HT):	0.597	Drug-induced Liver Injury (DILI):	0.038
AMES Toxicity:	0.366	Rat Oral Acute Toxicity:	0.189
Maximum Recommended Daily Dose:	0.653	Skin Sensitization:	0.842
Carcinogencity:	0.733	Eye Corrosion:	0.004
Eye Irritation:	0.58	Respiratory Toxicity:	0.885
Drug-induced Neurotoxicity:	0.024	Ototoxicity:	0.44
Hematotoxicity:	0.316	Drug-induced Nephrotoxicity:	0.329
Genotoxicity:	0.256	RPMI-8226 Immunitoxicity:	0.068
A549 Cytotoxicity:	0.271	Hek293 Cytotoxicity:	0.294
BCF:	2.307 ? 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:	4.84 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.181 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.632 ? 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
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075773]
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608862]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18464091]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558747]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	stem bark	Pangradin village, Jasinga, West Java, Indonesia	2005-AUG	PMID[19839614]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20817450]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[24555285]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717154]
NPO41067	Trigona minor	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28783356]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	fruit hulls	Madras, Tamil Nadu, India	1993-MAR	PMID[9213587]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8354	Aster bellidiastrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9717	Wibelia divaricata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8354	Aster bellidiastrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9717	Wibelia divaricata	Species	Davalliaceae	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	1
Inhibition	1
PC50	1

Activity Type	# Activity
Cell line	1
Organism	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	PC50	=	16.4	uM	PMID[28783356]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	5900.0	nM	PMID[12608862]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	21.0	%	PMID[12608862]

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 NPC22133 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	19631
0.1-0.2	25807
0.2-0.3	3847
0.3-0.4	422
0.4-0.5	103
0.5-0.6	15
0.6-0.7	27
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.76	Intermediate Similarity	NPC82623
0.7222	Intermediate Similarity	NPC134481
0.7115	Intermediate Similarity	NPC273366
0.6923	Remote Similarity	NPC604180
0.6852	Remote Similarity	NPC76518
0.6667	Remote Similarity	NPC18384
0.6667	Remote Similarity	NPC41577
0.6607	Remote Similarity	NPC89747
0.6604	Remote Similarity	NPC255650
0.6604	Remote Similarity	NPC85346
0.6604	Remote Similarity	NPC65897
0.6604	Remote Similarity	NPC80237
0.6545	Remote Similarity	NPC472341
0.6538	Remote Similarity	NPC299948
0.6538	Remote Similarity	NPC241085
0.6538	Remote Similarity	NPC607543
0.6481	Remote Similarity	NPC195530
0.6429	Remote Similarity	NPC12722
0.6415	Remote Similarity	NPC331618
0.6415	Remote Similarity	NPC257191
0.6415	Remote Similarity	NPC196358
0.6316	Remote Similarity	NPC606508
0.6296	Remote Similarity	NPC200243
0.6296	Remote Similarity	NPC254509
0.6182	Remote Similarity	NPC470830
0.6182	Remote Similarity	NPC472342
0.6182	Remote Similarity	NPC479659
0.6102	Remote Similarity	NPC110923
0.6102	Remote Similarity	NPC74296
0.6034	Remote Similarity	NPC473238
0.5902	Remote Similarity	NPC195366
0.5902	Remote Similarity	NPC85379
0.5902	Remote Similarity	NPC144909
0.5902	Remote Similarity	NPC476304
0.5902	Remote Similarity	NPC114743
0.5833	Remote Similarity	NPC476186
0.5789	Remote Similarity	NPC473279
0.5738	Remote Similarity	NPC307776
0.5738	Remote Similarity	NPC483817
0.569	Remote Similarity	NPC67872
0.5517	Remote Similarity	NPC70982
0.5224	Remote Similarity	NPC603266
0.5167	Remote Similarity	NPC282275
0.5156	Remote Similarity	NPC482424
0.5082	Remote Similarity	NPC477858

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC22133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6938
0.1-0.2	2101
0.2-0.3	110
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