NPASS Compound

Natural Product: NPC301501

Natural Product ID	NPC301501
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Globospiramine
IUPAC Name	n.a.
Synonyms	Globospiramine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1797183
PubChem CID	53329268
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002755] Aspidospermatan-type alkaloids

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 102114 0 0 0 0 0 0 0 0999 V2000 0.8262 3.7175 -3.6903 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0255 2.9613 -2.5170 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3433 2.7374 -2.1034 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4006 3.2458 -2.8294 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7166 3.0545 -2.4659 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9398 2.3149 -1.3171 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9145 1.7928 -0.5682 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6258 2.0083 -0.9676 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7076 1.3879 -0.0713 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2945 1.2911 0.0540 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2288 -0.0443 0.4956 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7559 -0.8567 1.3166 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1124 -0.7570 0.7284 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1417 -1.7111 1.2059 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3615 -1.4688 0.2991 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0014 -1.5529 -1.1497 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2841 -2.0349 -1.7633 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7460 -1.7295 -2.8928 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8393 -2.8730 -0.8350 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4062 -2.5084 0.4842 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6309 -2.0368 1.2177 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3355 -1.1389 2.3677 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2184 -0.2497 2.1388 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4640 1.0888 2.5691 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4627 1.9062 1.7939 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9458 0.9924 0.6730 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5362 0.6966 0.9322 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9088 -0.1226 0.7052 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3976 0.2191 1.3973 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7451 0.2096 0.8443 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6161 0.0998 2.0781 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6419 -0.4799 3.0841 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4853 -0.7762 2.4057 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1571 1.3812 -0.0266 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6575 1.2391 -0.1083 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1190 0.0416 -0.4283 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2264 -1.0996 -0.7019 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8643 -1.1180 -2.2132 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3779 -1.5324 -2.1865 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9346 -0.7821 -1.0845 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9133 -1.0344 -0.0480 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 -0.9135 -0.6931 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2585 -2.2558 -0.4727 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0747 -2.2784 -0.4181 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7820 -3.6408 -0.2472 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7944 -4.5706 -0.1491 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1229 -4.1979 -0.2150 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3953 -2.8558 -0.3800 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3896 -1.8923 -0.4791 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4391 -0.4558 -0.4989 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5246 2.3498 0.1498 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7953 2.2643 0.0901 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0074 3.5933 0.4832 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9069 4.6529 0.7273 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2562 3.6442 -3.9842 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3810 3.2241 -4.5134 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1328 4.7746 -3.5606 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1640 3.8181 -3.7221 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5134 3.4668 -3.0577 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9963 2.1732 -1.0435 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0560 2.1356 0.6990 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1481 1.5064 -0.9630 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7637 -0.4106 2.3327 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3657 -1.8784 1.4124 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9984 -0.9441 -0.3816 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7673 -2.7315 1.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4483 -1.4414 2.2294 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6768 -0.6169 -1.6061 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2060 -2.3235 -1.2770 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9878 -3.4488 0.9228 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1445 -2.9445 1.6130 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3832 -1.5718 0.5171 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1719 -1.7097 3.2953 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2346 -0.4950 2.5371 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2279 1.1822 3.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5068 1.4040 2.3740 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0185 2.7375 1.3198 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6253 2.2634 2.4248 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1872 1.0741 1.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8161 0.1270 0.1331 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1457 1.1476 1.9914 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4903 -0.5588 1.9200 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9362 1.1262 2.3542 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0474 -1.4187 3.5270 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3826 0.2655 3.8753 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8003 1.1613 -1.0506 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8703 2.3526 0.3703 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0140 -0.1268 -2.6501 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4886 -1.9101 -2.6604 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3975 -2.6318 -2.0547 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9517 -1.2745 -3.1610 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6726 -1.9397 0.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0565 -0.5747 -1.5305 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0333 -2.8372 -0.3637 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7719 -3.9555 -0.1935 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6111 -5.6354 -0.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9239 -4.9437 -0.1387 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4081 -2.5084 -0.4379 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3424 0.0922 -0.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4543 5.4199 1.3879 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2343 5.1458 -0.2129 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8387 4.3110 1.2397 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 11 10 1 6 11 12 1 0 12 13 1 0 13 14 1 0 15 14 1 1 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 26 25 1 1 26 27 1 0 26 28 1 0 11 29 1 0 29 30 1 0 30 31 1 1 31 32 1 0 32 33 1 0 30 34 1 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 1 6 38 39 1 0 39 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 37 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 35 51 1 0 51 52 2 0 51 53 1 0 53 54 1 0 8 3 1 0 27 9 1 0 33 29 1 0 50 36 1 0 26 7 1 0 41 30 1 0 49 44 1 0 42 11 1 0 27 13 1 0 41 37 1 0 20 15 1 0 28 23 1 0 28 15 1 0 1 55 1 0 1 56 1 0 1 57 1 0 4 58 1 0 5 59 1 0 6 60 1 0 10 61 1 0 10 62 1 0 12 63 1 0 12 64 1 0 13 65 1 6 14 66 1 0 14 67 1 0 16 68 1 0 16 69 1 0 20 70 1 1 21 71 1 0 21 72 1 0 22 73 1 0 22 74 1 0 24 75 1 0 24 76 1 0 25 77 1 0 25 78 1 0 27 79 1 1 28 80 1 6 29 81 1 1 31 82 1 0 31 83 1 0 32 84 1 0 32 85 1 0 34 86 1 0 34 87 1 0 38 88 1 0 38 89 1 0 39 90 1 0 39 91 1 0 41 92 1 1 42 93 1 6 43 94 1 0 45 95 1 0 46 96 1 0 47 97 1 0 48 98 1 0 50 99 1 0 54100 1 0 54101 1 0 54102 1 0 M END

Standard InCHIKey	YPRWDJLQPBDJAW-HHVNBPBNSA-N
Standard InCHI	InChI=1S/C43H48N4O7/c1-51-28-9-5-7-26-31(28)47-22-41(19-23-18-40-21-30(48)54-29(40)10-14-45-15-11-43(26,33(23)47)35(40)45)37-39(13-17-53-37)20-24(34(49)52-2)32-42(12-16-46(36(39)42)38(41)50)25-6-3-4-8-27(25)44-32/h3-9,23,29,33,35-38,44,50H,10-22H2,1-2H3/t23-,29-,33-,35-,36-,37+,38+,39-,40-,41-,42-,43-/m0/s1
SMILES	COc1cccc2c1N1C[C@@]3(C[C@@H]4C[C@]56CC(=O)O[C@H]5CCN5CC[C@]2([C@@H]14)[C@H]65)[C@H]1[C@@]2(CCO1)CC(=C1[C@]4(CCN([C@@H]24)[C@@H]3O)c2ccccc2N1)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	732.35	Volume:	722.84 ? Van der Waals volume.
Dense:	1.013	LogP:	2.425 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.598 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.171 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	60.0
TPSA:	113.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	13.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.442	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.227	Fsp³:	0.628
MCE-18:	344.143 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.549	Fluc inhibitor:	0.008 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.461 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.361 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.0	Promiscuous compounds:	0.391

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.634	MDCK Permeability:	-4.93
Pgp-inhibitor:	0.005	Pgp-substrate:	1.0
PAMPA:	0.0 ? 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%):	0.019	30% Bioavailability (F30%):	0.887
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988	MRP1:	0.99
Plasma Protein Binding (PPB):	95.808%	Volume Distribution (VD):	0.396
Fu:	3.705% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.953
OATP1B3 inhibitor:	0.921	BCRP inhibitor:	0.424
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.999	CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.398	CYP2D6-substrate:	0.938
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.022
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	1.0 ? 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):

6.101

Half-life (T1/2):

1.308

ADMET: Toxicity

hERG Blockers:	0.246	hERG Blockers (10um):	0.168
Human Hepatotoxicity (H-HT):	0.94	Drug-induced Liver Injury (DILI):	0.911
AMES Toxicity:	0.767	Rat Oral Acute Toxicity:	0.751
Maximum Recommended Daily Dose:	0.947	Skin Sensitization:	1.0
Carcinogencity:	0.775	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.96
Drug-induced Neurotoxicity:	0.823	Ototoxicity:	0.964
Hematotoxicity:	0.931	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.153
A549 Cytotoxicity:	0.843	Hek293 Cytotoxicity:	0.829
BCF:	0.777 ? 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:	3.766 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.668 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.959 ? 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
NPO32722	voacanga globosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21546135]

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	3
MIC	2

Activity Type	# Activity
Individual protein	3
Organism	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT67	Individual protein	Cholinesterase	Equus caballus	IC50	=	16400.0	nM	PMID[1336040]
NPT67	Individual protein	Cholinesterase	Equus caballus	IC50	=	16255.49	nM	PMID[20017493]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	94000.0	nM	PMID[18973387]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	4.0	ug.mL-1	PMID[19805556]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	5.2	ug.mL-1	PMID[10579870]

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 NPC301501 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	20774
0.1-0.2	28775
0.2-0.3	219
0.3-0.4	60
0.4-0.5	10
0.5-0.6	14
0.6-0.7	4
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8235	Intermediate Similarity	NPC139373
0.7459	Intermediate Similarity	NPC223242
0.687	Remote Similarity	NPC62560
0.6519	Remote Similarity	NPC469452
0.6304	Remote Similarity	NPC329932
0.6194	Remote Similarity	NPC208572
0.5971	Remote Similarity	NPC485976
0.5778	Remote Similarity	NPC18809
0.5778	Remote Similarity	NPC199826
0.5764	Remote Similarity	NPC485977
0.5674	Remote Similarity	NPC131977
0.5634	Remote Similarity	NPC469450
0.5547	Remote Similarity	NPC485978
0.5547	Remote Similarity	NPC485973
0.5448	Remote Similarity	NPC469451
0.517	Remote Similarity	NPC485972
0.5105	Remote Similarity	NPC485974
0.5105	Remote Similarity	NPC485979
0.5069	Remote Similarity	NPC208310
0.5069	Remote Similarity	NPC301174

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC301501 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4208
0.1-0.2	4908
0.2-0.3	34
0.3-0.4	0
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