NPASS Compound

Natural Product: NPC39082

Natural Product ID	NPC39082
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YCWGPALSXRBKTM-XGNRZNIMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101600075
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 85 88 0 0 0 0 0 0 0 0999 V2000 4.4828 -1.3018 -0.2166 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4685 -0.2092 0.0386 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7382 0.6299 1.2229 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0390 1.3894 1.2337 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2149 0.5281 1.1761 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1484 0.5606 0.2146 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9436 1.5566 -0.8571 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2946 -0.3447 0.2423 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4779 -1.1827 1.1328 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2109 -0.2412 -0.7931 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1195 -0.8089 -0.0455 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8247 -1.9112 0.9264 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3147 -2.1197 0.6861 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1416 -1.0164 -0.2068 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1577 -1.4085 -1.6517 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4250 -0.3851 0.1053 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3805 -0.9443 0.8181 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6687 -0.2373 1.0926 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0033 0.5157 -0.1802 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4142 0.9408 -0.3018 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2934 -0.3003 -0.2238 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9144 1.8996 0.7199 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6049 1.4925 -1.7054 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6486 2.6030 -1.9762 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1926 2.2446 -1.7579 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9898 1.5743 -0.4152 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9742 2.6402 0.6609 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6352 0.9653 -0.4124 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5870 1.6628 -0.8668 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8063 1.1722 -0.8899 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9305 0.0519 0.1037 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5829 0.5302 1.4687 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5021 0.4691 -2.6444 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1380 -3.3413 -0.0513 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5376 -4.4069 0.4816 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0069 -4.3117 1.6350 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6792 -5.6362 -0.3497 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9168 -2.2163 -0.5700 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1683 -1.0805 -1.0537 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9882 -1.6557 0.7060 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5605 0.4726 -0.8644 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9521 1.4420 1.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7140 0.0533 2.1939 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0564 1.9370 2.2265 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0522 2.2170 0.4921 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3845 -0.2019 1.9548 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0912 1.2371 -1.4862 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8321 2.5834 -0.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8429 1.5031 -1.5244 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1598 -0.5638 -0.7391 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9872 -1.3072 -1.0661 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9401 -1.6414 1.9902 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3816 -2.8299 0.6530 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1824 -2.2311 1.6414 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4330 -2.3294 -1.8777 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2150 -1.6872 -1.9471 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1381 -0.6411 -2.3631 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2433 -1.9213 1.2139 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6548 0.3696 1.9933 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4438 -1.0219 1.1995 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8396 -0.2512 -1.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5554 -0.5509 0.8238 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2434 -0.0402 -0.7348 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8551 -1.1526 -0.7771 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7376 1.5006 1.7404 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0412 1.9123 0.6228 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6094 2.9436 0.5826 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6215 1.8896 -1.7589 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9396 3.5229 -1.4518 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7328 2.8462 -3.0762 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8834 1.5614 -2.5464 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6512 3.2180 -1.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5063 2.3554 1.5759 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9222 2.8783 1.0001 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3334 3.5958 0.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7817 2.6541 -1.2401 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2204 0.9783 -1.8786 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4444 2.0144 -0.4772 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4857 0.3048 1.7657 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2043 0.2128 2.2935 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5930 1.6621 1.4669 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3819 -0.0089 -2.7375 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2110 -5.5216 -1.3359 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7621 -5.8560 -0.5397 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2061 -6.4749 0.1749 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 2 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 2 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 1 26 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 1 23 33 1 0 13 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 31 11 1 0 31 14 1 0 28 16 1 0 26 19 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 6 3 42 1 0 3 43 1 0 4 44 1 0 4 45 1 0 5 46 1 0 7 47 1 0 7 48 1 0 7 49 1 0 10 50 1 0 11 51 1 6 12 52 1 0 12 53 1 0 13 54 1 1 15 55 1 0 15 56 1 0 15 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 29 76 1 0 30 77 1 0 30 78 1 0 32 79 1 0 32 80 1 0 32 81 1 0 33 82 1 0 37 83 1 0 37 84 1 0 37 85 1 0 M END

Standard InCHIKey	YCWGPALSXRBKTM-XGNRZNIMSA-N
Standard InCHI	InChI=1S/C32H48O5/c1-19(10-9-11-20(2)28(35)36)24-18-27(37-21(3)33)32(8)23-12-13-25-29(4,5)26(34)15-16-30(25,6)22(23)14-17-31(24,32)7/h11-12,14,19,24-27,34H,9-10,13,15-18H2,1-8H3,(H,35,36)/b20-11+/t19-,24-,25+,26-,27+,30-,31-,32-/m1/s1
SMILES	C[C@H](CC/C=C(C)/C(=O)O)[C@H]1C[C@@H]([C@@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](CC[C@]4(C)C3=CC[C@]12C)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.35	Volume:	558.571 ? Van der Waals volume.
Dense:	0.917	LogP:	4.441 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.715 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.783 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	23.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.3	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.11	Fsp³:	0.75
MCE-18:	83.786 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.803	Fluc inhibitor:	0.02 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.06 ? 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:	0.433	Promiscuous compounds:	0.264

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.141	MDCK Permeability:	-4.861
Pgp-inhibitor:	0.634	Pgp-substrate:	0.027
PAMPA:	0.936 ? 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):	0.009
20% Bioavailability (F20%):	0.925	30% Bioavailability (F30%):	0.766
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.995
Plasma Protein Binding (PPB):	84.783%	Volume Distribution (VD):	-0.552
Fu:	10.006% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.07
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.308	CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.022	CYP3A4-substrate:	0.137
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.99
HLM stability:	0.511 ? 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):

5.247

Half-life (T1/2):

0.645

ADMET: Toxicity

hERG Blockers:	0.047	hERG Blockers (10um):	0.063
Human Hepatotoxicity (H-HT):	0.68	Drug-induced Liver Injury (DILI):	0.708
AMES Toxicity:	0.174	Rat Oral Acute Toxicity:	0.31
Maximum Recommended Daily Dose:	0.457	Skin Sensitization:	0.946
Carcinogencity:	0.325	Eye Corrosion:	0.006
Eye Irritation:	0.256	Respiratory Toxicity:	0.732
Drug-induced Neurotoxicity:	0.061	Ototoxicity:	0.688
Hematotoxicity:	0.397	Drug-induced Nephrotoxicity:	0.676
Genotoxicity:	0.867	RPMI-8226 Immunitoxicity:	0.061
A549 Cytotoxicity:	0.318	Hek293 Cytotoxicity:	0.224
BCF:	0.588 ? 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:	3.602 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.426 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.607 ? 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
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO40518	Ganoderma australe BCC 22314	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]
NPO40520	Ganoderma sp. BCC 60695	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]
NPO40519	Ganoderma orbiforme BCC 22325	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	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	2
MIC	1

Activity Type	# Activity
Individual protein	1
Cell line	1
Organism	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	IC50	=	25000.0	nM	PMID[31035236]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	94000.0	nM	PMID[28504879]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	25.0	ug.mL-1	PMID[28504879]

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 NPC39082 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	17450
0.1-0.2	25553
0.2-0.3	6240
0.3-0.4	501
0.4-0.5	65
0.5-0.6	31
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
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	NPC610107
0.8088	Intermediate Similarity	NPC136044
0.7746	Intermediate Similarity	NPC137552
0.7746	Intermediate Similarity	NPC99411
0.7714	Intermediate Similarity	NPC58410
0.7101	Intermediate Similarity	NPC212948
0.7	Intermediate Similarity	NPC138536
0.6944	Remote Similarity	NPC489801
0.6711	Remote Similarity	NPC94393
0.6267	Remote Similarity	NPC141401
0.6267	Remote Similarity	NPC478313
0.6267	Remote Similarity	NPC489790
0.6184	Remote Similarity	NPC85742
0.6184	Remote Similarity	NPC22421
0.5974	Remote Similarity	NPC489791
0.5949	Remote Similarity	NPC92022
0.5875	Remote Similarity	NPC478303
0.5714	Remote Similarity	NPC478308
0.5663	Remote Similarity	NPC198442
0.5584	Remote Similarity	NPC214697
0.557	Remote Similarity	NPC285702
0.557	Remote Similarity	NPC166745
0.557	Remote Similarity	NPC235464
0.55	Remote Similarity	NPC489802
0.55	Remote Similarity	NPC478301
0.5432	Remote Similarity	NPC489803
0.5432	Remote Similarity	NPC489804
0.5333	Remote Similarity	NPC475772
0.5278	Remote Similarity	NPC205455
0.527	Remote Similarity	NPC202389
0.5205	Remote Similarity	NPC147568
0.5195	Remote Similarity	NPC84271
0.5195	Remote Similarity	NPC102414
0.519	Remote Similarity	NPC469406
0.519	Remote Similarity	NPC601194
0.5176	Remote Similarity	NPC489793
0.5128	Remote Similarity	NPC87552
0.5119	Remote Similarity	NPC489796
0.5116	Remote Similarity	NPC478306
0.5116	Remote Similarity	NPC137291
0.5063	Remote Similarity	NPC472240
0.5063	Remote Similarity	NPC262858
0.5062	Remote Similarity	NPC276127
0.5062	Remote Similarity	NPC478307
0.5059	Remote Similarity	NPC489799

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC39082 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5857
0.1-0.2	3166
0.2-0.3	121
0.3-0.4	6
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