NPASS Compound

Natural Product: NPC58208

Natural Product ID	NPC58208
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JNYKCGNCXSSXEF-NQDUAKDMSA-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:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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 78 81 0 0 0 0 0 0 0 0999 V2000 7.4279 -1.1785 -0.4157 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1715 -0.8621 0.4110 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4201 0.2871 -0.1033 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1678 0.1096 -0.4956 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3410 -1.0617 -0.5211 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0791 -1.0760 0.2912 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5648 -0.8777 1.7321 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0332 -0.1283 -0.1348 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6215 -0.3918 -1.5573 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1391 -1.6921 -1.4334 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0817 -1.3350 -0.3123 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3543 -0.7348 -0.8180 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1601 -1.5701 -1.7487 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3121 -0.6710 -2.1711 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0052 -0.0286 -1.2484 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1160 0.8396 -1.6515 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5785 1.8272 -0.6375 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6879 1.0909 0.6831 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2785 0.7786 1.1084 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6402 -0.2194 0.1639 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2790 -1.5695 0.5628 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1566 -0.3111 0.3846 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5003 0.9756 0.8260 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0582 1.0810 0.3894 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3244 -0.2686 0.4973 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3392 -0.5569 1.9601 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8401 2.2738 -0.9874 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0667 1.6539 -0.1698 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1224 1.7418 -1.2291 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5197 2.1150 1.1914 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8956 -2.1192 0.0077 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2146 -0.4103 -0.2768 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1908 -1.4317 -1.4503 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6564 -1.8032 0.5213 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6188 -0.5064 1.3968 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6917 1.0456 -0.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9151 -1.9737 -0.2864 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0332 -1.2867 -1.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6421 -2.0875 0.2858 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6911 0.1636 2.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0538 -1.5335 2.4635 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6200 -1.3091 1.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3387 0.9497 -0.0068 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3648 -0.4773 -2.3108 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1247 0.3517 -1.9246 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6312 -1.8319 -2.4144 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4645 -2.5786 -1.2699 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2997 -2.2101 0.3258 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0819 0.1928 -1.4073 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5171 -2.5141 -1.3285 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6250 -1.7948 -2.6740 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5814 -0.5427 -3.2140 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9910 0.2071 -1.9575 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7813 1.4134 -2.5476 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8556 2.6552 -0.5176 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3326 0.2210 0.5793 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1406 1.7837 1.4107 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7504 1.7175 1.2255 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3462 0.2882 2.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4944 -2.1984 1.0761 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6431 -2.1330 -0.2923 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0909 -1.4623 1.2788 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0117 -1.1517 1.1267 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0123 1.7832 0.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6746 1.2333 1.8763 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8953 1.6021 -0.5410 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5590 1.7174 1.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3008 -1.5977 2.2449 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3790 0.1351 2.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3091 -0.1782 2.4186 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8561 2.7708 -1.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2682 2.3642 -0.4640 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1128 0.9019 -1.9536 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9825 2.6547 -1.8851 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1513 1.9207 -0.7966 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3807 3.2145 1.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9285 1.6442 1.9941 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6274 1.9595 1.3376 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 17 27 1 0 3 28 1 0 28 29 1 0 28 30 1 0 25 8 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 2 35 1 0 4 36 1 0 5 37 1 0 5 38 1 0 6 39 1 1 7 40 1 0 7 41 1 0 7 42 1 0 8 43 1 6 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 1 12 49 1 6 13 50 1 0 13 51 1 0 14 52 1 0 16 53 1 0 16 54 1 0 17 55 1 1 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 21 60 1 0 21 61 1 0 21 62 1 0 22 63 1 1 23 64 1 0 23 65 1 0 24 66 1 0 24 67 1 0 26 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 M END

Standard InCHIKey	JNYKCGNCXSSXEF-NQDUAKDMSA-N
Standard InCHI	InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h9-10,19-20,23-27,30H,7-8,11-18H2,1-6H3/b21-9+/t20-,23+,24-,25-,26-,27-,28+,29-/m1/s1
SMILES	CC/C(=CC[C@@H](C)[C@H]1CC[C@@H]2[C@H]3CC=C4C[C@H](CC[C@]4(C)[C@@H]3CC[C@]12C)O)/C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.37	Volume:	479.432 ? Van der Waals volume.
Dense:	0.86	LogP:	8.007 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.489 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.471 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	21.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.454	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.566	Fsp³:	0.862
MCE-18:	69.0 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.989	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.76	Promiscuous compounds:	0.02

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.921	MDCK Permeability:	-4.898
Pgp-inhibitor:	0.943	Pgp-substrate:	0.004
PAMPA:	0.004 ? 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%):	0.318	30% Bioavailability (F30%):	0.343
50% Bioavailability (F50%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.485
Plasma Protein Binding (PPB):	96.326%	Volume Distribution (VD):	-0.013
Fu:	4.354% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.617
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.581	CYP2C19-substrate:	0.329
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.981
CYP3A4-inhibitor:	0.963	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

11.579

Half-life (T1/2):

0.386

ADMET: Toxicity

hERG Blockers:	0.073	hERG Blockers (10um):	0.34
Human Hepatotoxicity (H-HT):	0.659	Drug-induced Liver Injury (DILI):	0.146
AMES Toxicity:	0.064	Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.256	Skin Sensitization:	0.979
Carcinogencity:	0.541	Eye Corrosion:	0.165
Eye Irritation:	0.95	Respiratory Toxicity:	0.923
Drug-induced Neurotoxicity:	0.156	Ototoxicity:	0.446
Hematotoxicity:	0.232	Drug-induced Nephrotoxicity:	0.552
Genotoxicity:	0.026	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.229	Hek293 Cytotoxicity:	0.405
BCF:	2.777 ? 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:	4.382 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.106 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.008 ? 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
NPO4862	Westiellopsis prolifica	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1602299]
NPO11532	Bidens parviflora	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16880667]
NPO14386	Piper hostmannianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO10561	Mentha suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36432812]
NPO10561	Mentha suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37836777]
NPO10561	Mentha suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38560258]
NPO4862	Westiellopsis prolifica	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11073	Alpinia formosana	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21147	Anisocycla grandidieri	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3577	Bambusa tulda	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11532	Bidens parviflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9025	Croton balsamifer	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13993	Dimelaena thysanota	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14583	Elsholtzia stauntonii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14603	Flindersia australis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8641	Haemanthus tigrinus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12589	Heliotropium angiospermum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10561	Mentha suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO805	Myrmicaria opaciventris	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1421	Papaver hybrid	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6627	Pinus bungeana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14386	Piper hostmannianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10834	Protea compacta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11334	Rubus moluccanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13898	Typhonium flagelliforme	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6627	Pinus bungeana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11532	Bidens parviflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10561	Mentha suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6627	Pinus bungeana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3577	Bambusa tulda	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6627	Pinus bungeana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14386	Piper hostmannianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14583	Elsholtzia stauntonii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13993	Dimelaena thysanota	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11532	Bidens parviflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12589	Heliotropium angiospermum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO805	Myrmicaria opaciventris	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14603	Flindersia australis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4862	Westiellopsis prolifica	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21147	Anisocycla grandidieri	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13898	Typhonium flagelliforme	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1421	Papaver hybrid	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8641	Haemanthus tigrinus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11334	Rubus moluccanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10561	Mentha suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10834	Protea compacta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11073	Alpinia formosana	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9025	Croton balsamifer	Species	Euphorbiaceae	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 NPC58208 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	24683
0.1-0.2	21216
0.2-0.3	3564
0.3-0.4	252
0.4-0.5	64
0.5-0.6	34
0.6-0.7	17
0.7-0.8	2
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC107059
0.8235	Intermediate Similarity	NPC472265
0.8125	Intermediate Similarity	NPC162742
0.8125	Intermediate Similarity	NPC304309
0.8125	Intermediate Similarity	NPC470228
0.8	Intermediate Similarity	NPC134847
0.7959	Intermediate Similarity	NPC22105
0.7959	Intermediate Similarity	NPC34019
0.7843	Intermediate Similarity	NPC264245
0.78	Intermediate Similarity	NPC136188
0.78	Intermediate Similarity	NPC28657
0.78	Intermediate Similarity	NPC474216
0.7647	Intermediate Similarity	NPC230301
0.7647	Intermediate Similarity	NPC198968
0.7647	Intermediate Similarity	NPC285893
0.75	Intermediate Similarity	NPC241290
0.75	Intermediate Similarity	NPC164840
0.75	Intermediate Similarity	NPC484739
0.75	Intermediate Similarity	NPC209944
0.75	Intermediate Similarity	NPC155986
0.7358	Intermediate Similarity	NPC321381
0.7255	Intermediate Similarity	NPC600590
0.7222	Intermediate Similarity	NPC59453
0.7143	Intermediate Similarity	NPC47761
0.7115	Intermediate Similarity	NPC154330
0.7091	Intermediate Similarity	NPC603646
0.6981	Remote Similarity	NPC113733
0.6964	Remote Similarity	NPC473943
0.6964	Remote Similarity	NPC155011
0.6923	Remote Similarity	NPC221758
0.6842	Remote Similarity	NPC488870
0.6607	Remote Similarity	NPC33913
0.6545	Remote Similarity	NPC51014
0.6491	Remote Similarity	NPC477522
0.6429	Remote Similarity	NPC328714
0.6379	Remote Similarity	NPC243985
0.6379	Remote Similarity	NPC280710
0.6379	Remote Similarity	NPC240650
0.6316	Remote Similarity	NPC318495
0.6275	Remote Similarity	NPC96319
0.6271	Remote Similarity	NPC474164
0.6182	Remote Similarity	NPC328313
0.614	Remote Similarity	NPC87604
0.5968	Remote Similarity	NPC601043
0.5968	Remote Similarity	NPC605412
0.5763	Remote Similarity	NPC1272
0.5763	Remote Similarity	NPC470614
0.5714	Remote Similarity	NPC151519
0.5614	Remote Similarity	NPC20688
0.5517	Remote Similarity	NPC76879
0.5303	Remote Similarity	NPC91604
0.5263	Remote Similarity	NPC81306
0.5254	Remote Similarity	NPC84694
0.5254	Remote Similarity	NPC143182
0.5231	Remote Similarity	NPC176012
0.5161	Remote Similarity	NPC474752
0.5161	Remote Similarity	NPC19607
0.5161	Remote Similarity	NPC474683
0.5152	Remote Similarity	NPC5985
0.5147	Remote Similarity	NPC235126
0.5147	Remote Similarity	NPC309493
0.5147	Remote Similarity	NPC242419
0.5085	Remote Similarity	NPC109546
0.5085	Remote Similarity	NPC189972
0.5085	Remote Similarity	NPC317458
0.5085	Remote Similarity	NPC47982
0.5082	Remote Similarity	NPC31564
0.5082	Remote Similarity	NPC145879
0.5082	Remote Similarity	NPC26959
0.5077	Remote Similarity	NPC474970
0.5077	Remote Similarity	NPC474349
0.5077	Remote Similarity	NPC474189
0.5072	Remote Similarity	NPC147835
0.5072	Remote Similarity	NPC253645
0.5072	Remote Similarity	NPC85001
0.5072	Remote Similarity	NPC95920
0.507	Remote Similarity	NPC3715

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC58208 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7812
0.1-0.2	1173
0.2-0.3	130
0.3-0.4	28
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
0.7-0.8	2
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
0.78	Intermediate Similarity	NPD6942	Phase 4
0.7647	Intermediate Similarity	NPD7339	Approved
0.6923	Remote Similarity	NPD4786	Phase 1
0.6275	Remote Similarity	NPD3701	Pre-clinical
0.5714	Remote Similarity	NPD3667	Phase 4

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