NPASS Compound

Natural Product: NPC478305

Natural Product ID	NPC478305
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GXKWNYCHKLAQPO-KGGJRMPESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	127032138
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 102105 0 0 0 0 0 0 0 0999 V2000 -5.0686 -3.0212 -2.4101 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9131 -3.0277 -1.1915 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6203 -2.2837 -0.1631 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3749 -1.4128 -0.2742 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7658 0.0334 -0.1289 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7613 1.0687 -0.2286 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5403 2.4206 -0.0277 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5036 1.2113 0.4250 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3038 1.2764 1.8756 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7628 1.2682 2.1066 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2330 1.4156 0.7234 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3013 2.8514 0.3508 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1122 0.8142 0.4553 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3033 0.0554 -0.6106 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2657 -0.2864 -1.6389 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9745 0.5425 -1.4484 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2604 0.5178 -0.0013 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1878 -0.8499 0.5987 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6554 -0.5524 -0.8424 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5992 -1.9439 -0.2692 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9914 -0.7102 -2.3033 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2687 -1.5263 -2.3470 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4054 -0.9639 -1.5707 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0924 0.1306 -0.6277 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8991 -0.0979 0.6604 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6818 1.4273 -1.2138 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6711 0.3292 -0.2348 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4229 0.2261 1.2563 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1731 1.1534 1.4381 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7897 2.4024 1.1582 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9098 3.1562 2.2878 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1527 -1.9971 -0.8996 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4275 -2.3631 -1.2266 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9795 -1.7411 -2.1906 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1634 -3.4356 -0.5083 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4665 2.3277 2.9934 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0188 2.0528 4.2686 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1145 0.8293 4.6075 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3156 3.0796 5.2663 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7544 0.2072 -1.1842 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0994 0.3477 -0.9095 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5559 0.3358 0.2541 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0387 0.5191 -2.0375 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0991 -3.9045 -1.1775 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3762 -4.6180 -2.1710 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9431 -3.9798 -0.0929 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9916 -2.0002 -2.8242 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0361 -3.4018 -2.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4589 -3.7305 -3.1712 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2121 -2.2709 0.7233 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8273 -1.6324 -1.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8103 -1.7671 0.6453 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3959 0.0558 0.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5375 1.1536 -1.3639 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7245 2.5742 1.0508 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4259 2.4411 -0.6618 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8857 3.2574 -0.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1975 2.3287 0.1094 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6843 2.2585 2.2942 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6960 0.5152 2.5233 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4980 0.3152 2.6184 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5561 3.0946 -0.6834 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7438 3.2762 0.4716 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8688 3.4824 1.1032 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6694 -0.1385 -2.6760 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0146 -1.3466 -1.5496 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7935 0.0978 -2.0664 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7799 1.5211 -1.8741 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5108 -1.6076 -0.1390 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8062 -0.9597 1.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1664 -1.1351 0.9275 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9898 -2.0088 0.6486 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0871 -2.5879 -1.0268 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5872 -2.3547 -0.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2108 -1.3897 -2.7650 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1066 0.2265 -2.8476 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0619 -2.5598 -1.9640 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4832 -1.6794 -3.4307 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1393 -0.6027 -2.3584 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9298 -0.4274 0.3322 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0599 0.9055 1.1002 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4290 -0.8291 1.3158 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6967 1.6056 -0.8653 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0232 2.2830 -1.0246 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7333 1.3192 -2.3348 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4086 1.3734 -0.5189 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1994 0.6913 1.8779 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2369 -0.7704 1.6320 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8422 1.0582 2.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5125 2.6101 3.0438 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9212 3.4690 2.6493 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4196 4.1112 1.9906 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5123 -4.3351 -0.3503 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0580 -3.7340 -1.1030 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5173 -3.1296 0.4815 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0525 2.6596 5.9769 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6164 3.3171 5.8405 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7476 3.9935 4.8094 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8864 -0.2408 -2.8303 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7678 1.5073 -2.5123 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0877 0.6121 -1.7248 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6141 -4.7592 -0.0216 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 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 6 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 14 19 1 0 19 20 1 1 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 23 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 10 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 5 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 2 44 1 0 44 45 2 0 44 46 1 0 17 8 1 0 27 19 1 0 17 11 1 0 29 13 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 1 6 54 1 6 7 55 1 0 7 56 1 0 7 57 1 0 8 58 1 6 9 59 1 0 9 60 1 0 10 61 1 1 12 62 1 0 12 63 1 0 12 64 1 0 15 65 1 0 15 66 1 0 16 67 1 0 16 68 1 0 18 69 1 0 18 70 1 0 18 71 1 0 20 72 1 0 20 73 1 0 20 74 1 0 21 75 1 0 21 76 1 0 22 77 1 0 22 78 1 0 23 79 1 6 25 80 1 0 25 81 1 0 25 82 1 0 26 83 1 0 26 84 1 0 26 85 1 0 27 86 1 6 28 87 1 0 28 88 1 0 29 89 1 1 31 90 1 0 31 91 1 0 31 92 1 0 35 93 1 0 35 94 1 0 35 95 1 0 39 96 1 0 39 97 1 0 39 98 1 0 43 99 1 0 43100 1 0 43101 1 0 46102 1 0 M END

Standard InCHIKey	GXKWNYCHKLAQPO-KGGJRMPESA-N
Standard InCHI	InChI=1S/C37H56O9/c1-20(33(41)42)12-13-27(44-22(3)38)21(2)26-18-31(46-24(5)40)37(10)32-25(14-17-36(26,37)9)35(8)16-15-30(45-23(4)39)34(6,7)29(35)19-28(32)43-11/h12,21,26-31H,13-19H2,1-11H3,(H,41,42)/b20-12+/t21-,26+,27-,28+,29-,30-,31-,35+,36+,37-/m0/s1
SMILES	C/C(=CC[C@@H]([C@@H](C)[C@H]1C[C@@H]([C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1C[C@H]3OC)OC(=O)C)OC(=O)C)OC(=O)C)/C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	644.39	Volume:	677.575 ? Van der Waals volume.
Dense:	0.951	LogP:	2.749 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.696 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.27 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	25.0
TPSA:	125.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.125	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.493	Fsp³:	0.784
MCE-18:	93.273 ? 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:	0.936	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.361	Promiscuous compounds:	0.53

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.158	MDCK Permeability:	-4.86
Pgp-inhibitor:	1.0	Pgp-substrate:	0.017
PAMPA:	0.705 ? 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):	0.049
20% Bioavailability (F20%):	0.989	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	75.791%	Volume Distribution (VD):	-0.659
Fu:	13.962% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.003
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.054	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.989
HLM stability:	0.915 ? 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):

3.814

Half-life (T1/2):

0.676

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.022
Human Hepatotoxicity (H-HT):	0.686	Drug-induced Liver Injury (DILI):	0.954
AMES Toxicity:	0.207	Rat Oral Acute Toxicity:	0.297
Maximum Recommended Daily Dose:	0.349	Skin Sensitization:	0.932
Carcinogencity:	0.505	Eye Corrosion:	0.0
Eye Irritation:	0.046	Respiratory Toxicity:	0.319
Drug-induced Neurotoxicity:	0.056	Ototoxicity:	0.587
Hematotoxicity:	0.701	Drug-induced Nephrotoxicity:	0.72
Genotoxicity:	0.973	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.251	Hek293 Cytotoxicity:	0.192
BCF:	0.45 ? 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:	3.651 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.758 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.914 ? 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
NPO40141	Ganoderma sp. BCC 16642	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26716912]
NPO40519	Ganoderma orbiforme BCC 22325	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]
NPO40518	Ganoderma australe BCC 22314	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]
NPO40141	Ganoderma sp. BCC 16642	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
MIC	2
IC50	2

Activity Type	# Activity
Cell line	2
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
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	26000.0	nM	PMID[26716912]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	26000.0	nM	PMID[28504879]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	12.5	ug.mL-1	PMID[26716912]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12.5	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 NPC478305 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	21765
0.1-0.2	25457
0.2-0.3	2463
0.3-0.4	110
0.4-0.5	29
0.5-0.6	12
0.6-0.7	9
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC52776
0.8971	High Similarity	NPC610168
0.8028	Intermediate Similarity	NPC489788
0.8028	Intermediate Similarity	NPC299325
0.7945	Intermediate Similarity	NPC489805
0.7639	Intermediate Similarity	NPC489803
0.7639	Intermediate Similarity	NPC489804
0.7606	Intermediate Similarity	NPC478300
0.75	Intermediate Similarity	NPC489809
0.7333	Intermediate Similarity	NPC478304
0.7333	Intermediate Similarity	NPC231673
0.6923	Remote Similarity	NPC489794
0.6667	Remote Similarity	NPC85742
0.6667	Remote Similarity	NPC22421
0.6364	Remote Similarity	NPC478301
0.6203	Remote Similarity	NPC478299
0.6154	Remote Similarity	NPC489807
0.6154	Remote Similarity	NPC478298
0.6125	Remote Similarity	NPC478311
0.6024	Remote Similarity	NPC478310
0.5926	Remote Similarity	NPC489795
0.5904	Remote Similarity	NPC478306
0.5904	Remote Similarity	NPC137291
0.5854	Remote Similarity	NPC489797
0.5769	Remote Similarity	NPC478308
0.5696	Remote Similarity	NPC276127
0.5696	Remote Similarity	NPC478307
0.5556	Remote Similarity	NPC58410
0.5542	Remote Similarity	NPC478303
0.5422	Remote Similarity	NPC92022
0.5412	Remote Similarity	NPC489793
0.506	Remote Similarity	NPC136044

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478305 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6219
0.1-0.2	2893
0.2-0.3	36
0.3-0.4	2
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